acetone O-benzyloxime -Drug Synthesis Database

【结构式】

【分子编号】53314

【品名】acetone O-benzyloxime

【CA登记号】n/a

【分子式】C₁₀H₁₃NO

【分子量】163.21936

【元素组成】C 73.59% H 8.03% N 8.58% O 9.8%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(III)

The reaction of 14C-labeled acetone (I) with O-benzylhydroxylamine (II) and pyridine in refluxing ethanol gives the corresponding oxime (III), which is methylated with MeLi and BF3.Et2O in toluene to yield labeled N-tert-butyl-O-benzylhydroxylamine (IV). The deprotection of (IV) by hydrogenation with H2 over Pd/C in methanol affords N-tert-butylhydroxylamine (V), which is finally condensed with benzaldehyde 2,4-disulfonic acid sodium salt (VI) in HOAc/water to give rise to the target imine oxide.

参考文献中间体

合成目标

【1】 Johansson, R.; Werner, R.; Syntheses of two [14C]-labeled disodium 4-[(N-tert-butylimino)methyl]benzene-1,3-disulfonate N-oxides. J Label Compd Radiopharm 2000, 43, 13, 1265.

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)	14640	O-benzylhydroxylamine; 1-[(aminooxy)methyl]benzene	622-33-3	C₇H₉NO	详情	详情
(II)	23199	2-Propanone; Acetone; beta-ketopropane; chevron acetone;propan-2-one； Dimethyl formaldehyde; Dimethyl ketone; dimethylketal; Ketone propane; Methyl ketone; Propanone; Pyroacetic acid; Pyroacetic ether	67-64-1	C₃H₆O	详情	详情
(II)	53313	acetone	67-64-1	C₃H₆O	详情	详情
(III)	53314	acetone O-benzyloxime	n/a	C₁₀H₁₃NO	详情	详情
(III)	53315	acetone O-benzyloxime	n/a	C₁₀H₁₃NO	详情	详情
(IV)	53316	1-{[(tert-butylamino)oxy]methyl}benzene; O-benzyl-N-(tert-butyl)hydroxylamine	n/a	C₁₁H₁₇NO	详情	详情
(IV)	53317	O-benzyl-N-(tert-butyl)hydroxylamine; 1-{[(tert-butylamino)oxy]methyl}benzene	n/a	C₁₁H₁₇NO	详情	详情
(V)	35455	N-(tert-butyl)hydroxylamine; 2-(hydroxyamino)-2-methylpropane		C₄H₁₁NO	详情	详情
(V)	53318	2-(hydroxyamino)-2-methylpropane; N-(tert-butyl)hydroxylamine	16649-50-6	C₄H₁₁NO	详情	详情
(VI)	37311	Benzaldehyde-2,4-disulfonic acid disodium; disodium 4-formyl-1,3-benzenedisulfonate	33513-44-9	C₇H₄Na₂O₇S₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

A stereoselective synthesis for the title 2'S isomer was also reported, employing (S)-1-mercapto-2-propanol (VII). Conversion of the chiral tosylate (IV) to the trityl sulfide (V) was achieved by treatment with the lithium thiolate of triphenylmethanethiol. The trityl group of (V) was then removed by iodine in MeOH, producing disulfide (VI). This was reduced with NaBH4 to the corresponding thiol (VII), which was subsequently added to brefeldin A (I), producing the desired sulfide isomer (VIII). Final oxidation of sulfide (VIII) with m-CPBA yielded the target sulfoxide.

参考文献中间体

合成目标

【1】 Fox, B.M.; et al.; Preparation and evaluation of sulfide derivatives of the antibiotic brefeldin A as potential prodrug candidates with enhanced aqueous solubilities. J Med Chem 2001, 44, 23, 3915.

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)	53314	acetone O-benzyloxime	n/a	C₁₀H₁₃NO	详情	详情
(IV)	53385	(2S)-2-hydroxypropyl 4-methylbenzenesulfonate	n/a	C₁₀H₁₄O₄S	详情	详情
(V)	53386	(2S)-1-(tritylsulfanyl)-2-propanol	n/a	C₂₂H₂₂OS	详情	详情
(VI)	53387	(2S)-1-{[(2S)-2-hydroxypropyl]disulfanyl}-2-propanol	n/a	C₆H₁₄O₂S₂	详情	详情
(VII)	53388	(2S)-1-sulfanyl-2-propanol	n/a	C₃H₈OS	详情	详情
(VIII)	53383	(1S,2R,6S,11aS,13S)-1,13-dihydroxy-2-{[(2S)-2-hydroxypropyl]sulfanyl}-6-methyl-1,2,3,6,7,8,9,11a,12,13,14,14a-dodecahydro-4H-cyclopenta[f]oxacyclotridecin-4-one	n/a	C₁₉H₃₂O₅S	详情	详情

Extended Information