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【结 构 式】 
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【分子编号】40598 【品名】amidosulfonoyl chloride 【CA登记号】7778-42-9 |
【 分 子 式 】H2ClNO2S 【 分 子 量 】115.54012 【元素组成】H 1.74% Cl 30.68% N 12.12% O 27.69% S 27.75% |
合成路线1
该中间体在本合成路线中的序号：(II)By esterification of 5,6,7,8-tetrahydronaphthalen-2-ol (I) with chlorosulfonamide (II) and NaH in DMF.
| 【1】 Potter, B.V.L.; Howarth, N.M.; Purohit, A.,; Reed, M.J.; Steroid sulphatase inhibitors: a new endocrine therapy. Drugs Fut 1994, 19, 7, 673. |
| 【2】 Reed, M.J.; Potter, B.V.L.; Purohit, A.,; Howarth, N.M.; Cooper, G.; Duncan, L.J.; Phosphonates and thiophosphonates as sulfate surrogates: Synthesis of estrone 3-methylthiophosphonate a potent inhibitor of estrone sulfatase. Bioorg Med Chem Lett 1993, 3, 2, 313-318. |
合成路线2
该中间体在本合成路线中的序号：(II)By esterification of estrone (I) with chlosulfonamide (II) and NaH in DMF.
| 【1】 Potter, B.V.L.; Howarth, N.M.; Purohit, A.,; Reed, M.J.; Steroid sulphatase inhibitors: a new endocrine therapy. Drugs Fut 1994, 19, 7, 673. |
| 【2】 Reed, M.J.; Potter, B.V.L.; Purohit, A.,; Howarth, N.M.; Cooper, G.; Duncan, L.J.; Phosphonates and thiophosphonates as sulfate surrogates: Synthesis of estrone 3-methylthiophosphonate a potent inhibitor of estrone sulfatase. Bioorg Med Chem Lett 1993, 3, 2, 313-318. |
合成路线3
该中间体在本合成路线中的序号：Grignard reagent (II), prepared from 4-tert-butylbenzyl bromide (I) and magnesium in Et2O, was condensed with estrone (III) to provide the 17-(tert-butylbenzyl)estradiol (IV). Subsequent reaction of (IV) with sulfamoyl chloride in the presence of 2,6-di-tert-butyl-4-methylpyridine (DBMP) yielded the title sulfamate ester.
| 【1】 Labrie, F.; Boivin, R.P.; Luu-The, V.; Ciobanu, L.C.; Poirier, D.; Potent inhibition of steroid sulfatase activity by 3-O-sulfamate 17alpha-Benzyl(or 4'-tert-butylbenzyl)estra-1,3,5(10)-trienes: Combination of two substituents at positions C3 and c17alpha of estradiol. J Med Chem 1999, 42, 12, 2280. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 40598 | amidosulfonoyl chloride | 7778-42-9 | H2ClNO2S | 详情 | 详情 | |
| (I) | 20588 | 1-(bromomethyl)-4-(tert-butyl)benzene | 18880-00-7 | C11H15Br | 详情 | 详情 |
| (II) | 34441 | bromo[4-(tert-butyl)benzyl]magnesium | C11H15BrMg | 详情 | 详情 | |
| (III) | 20468 | (8R,9S,13S,14S)-3-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-17H-cyclopenta[a]phenanthren-17-one | 53-16-7 | C18H22O2 | 详情 | 详情 |
| (IV) | 34442 | (8R,9S,13S,14S,17R)-17-[4-(tert-butyl)benzyl]-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol | C29H38O2 | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：Benzothiadiazine dioxide (II) was prepared by cyclization of methyl anthranylate (I) with sulfamoyl chloride, followed by aqueous NaOH. After silylation of (II) by means of hexamethyldisilazane, alkylation with benzyloxymethyl acetate (III) in the presence of boron trifluoride etherate produced the 3-(benzyloxymethyl)benzothiazine (IV). Further alkylation of (IV) with benzyl bromide in aqueous NaHCO3 furnished the title compound.
| 【1】 Esteban, A.I.; Martinez, A.; De Clercq, E.; Benzothiadiazine dioxide acyclonucleosides as lead compounds for the development of new agents against human cytomegalovirus and varicella-zoster virus infection. Bioorg Med Chem Lett 1997, 7, 8, 1031. |
| 【2】 Martinez, A.; et al.; Novel potential agents for human cytomegalovirus infection: Synthesis and antiviral activity evaluation of benzothiadiazine dioxide acyclonucleosides. J Med Chem 1999, 42, 7, 1145. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 12912 | 1-(Bromomethyl)benzene; Alpha-bromotoluene | 100-39-0 | C7H7Br | 详情 | 详情 | |
| 40598 | amidosulfonoyl chloride | 7778-42-9 | H2ClNO2S | 详情 | 详情 | |
| (I) | 11161 | methyl 2-aminobenzoate; Methyl anthranilate | 134-20-3 | C8H9NO2 | 详情 | 详情 |
| (II) | 34452 | 2lambda(6),1,3-benzothiadiazine-2,2,4(1H,3H)-trione | C7H6N2O3S | 详情 | 详情 | |
| (III) | 34453 | (benzyloxy)methyl acetate | C10H12O3 | 详情 | 详情 | |
| (IV) | 34454 | 3-[(benzyloxy)methyl]-2lambda(6),1,3-benzothiadiazine-2,2,4(1H,3H)-trione | C15H14N2O4S | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号：(V)Friedel-Crafts acylation of phenol (I) with nonanoyl chloride (II) in the presence of AlCl3 afforded ketone (III). Aminosulfonyl chloride (V) was prepared by decarboxylation of chlorosulfonyl isocyanate (IV) upon treatment with formic acid. Finally, condensation of the sodium phenolate of (III) with aminosulfonyl chloride (V) furnished the title sulfamate.
| 【1】 Ahmed, S.; et al.; Novel inhibitors of the enzyme estrone sulfatase (ES). Bioorg Med Chem Lett 2001, 11, 6, 841. |
| 【2】 Ahmed, S.; James, K.; Owen, C.P.; Patel, C.K.; Synthesis and biochemical evaluation of novel and potent inhibitors of the enzyme oestrone sulphatase (ES). J Steroid Biochem Mol Biol 2002, 80, 4-5, 419. |
| 【3】 Ahmed, S. (Kingston University); Sulphamate cpds.. WO 0104086 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 23540 | Phenol | 108-95-2 | C6H6O | 详情 | 详情 |
| (II) | 30296 | nonanoyl chloride | 764-85-2 | C9H17ClO | 详情 | 详情 |
| (III) | 50915 | 4-n-Nonanoylphenol; 4-Hydroxynonanophenone | 14392-69-9 | C15H22O2 | 详情 | 详情 |
| (IV) | 14101 | Chlorosulfonyl isocyanate | 1189-71-5 | CClNO3S | 详情 | 详情 |
| (V) | 40598 | amidosulfonoyl chloride | 7778-42-9 | H2ClNO2S | 详情 | 详情 |
合成路线6
该中间体在本合成路线中的序号：(II)
| 【1】 Liu K, Gao XS. Li Y, et al.2009. Process for preparation of doripenem. CN 101348485. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 67091 | 4-methoxybenzyl 3-((3-(aminomethyl)-4-(((4-nitrobenzyl)oxy)carbonyl)cyclopentyl)thio)-4-methyl-7-oxo-6-(1-((trimethylsilyl)oxy)ethyl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | C35H45N3O9SSi | 详情 | 详情 | |
| (II) | 40598 | amidosulfonoyl chloride | 7778-42-9 | H2ClNO2S | 详情 | 详情 |
| (III) | 67092 | nitro(phenyl)methyl 4-methyl-3-((1-(((4-nitrobenzyl)oxy)carbonyl)-5-((sulfamoylamino)methyl)pyrrolidin-3-yl)thio)-7-oxo-6-(1-((trimethylsilyl)oxy)ethyl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | C33H42N6O12S2Si | 详情 | 详情 | |
| (IV) | 67081 | nitro(phenyl)methyl 6-(1-hydroxyethyl)-4-methyl-3-((1-(((4-nitrobenzyl)oxy)carbonyl)-5-((sulfamoylamino)methyl)pyrrolidin-3-yl)thio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | C30H34N6O12S2 | 详情 | 详情 | |
| (V) | 67085 | 4-nitrobenzyl 6-(1-hydroxyethyl)-4-methyl-7-oxo-3-((5-((sulfamoylamino)methyl)pyrrolidin-3-yl)thio)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | C22H29N5O8S2 | 详情 | 详情 |