【结 构 式】 |
【分子编号】64443 【品名】tert-butyl 2-{3-[(hydroxyimino)methyl]phenoxy}acetate 【CA登记号】 |
【 分 子 式 】C13H17NO4 【 分 子 量 】251.28232 【元素组成】C 62.14% H 6.82% N 5.57% O 25.47% |
合成路线1
该中间体在本合成路线中的序号:(IV)Alkylation of 3-hydroxybenzaldehyde (I) with t-butyl bromoacetate (II) affords t butyl (3-formylphenoxy)acetate (III). Aldehyde (III) is then converted to oxime (IV) upon treatment with hydroxylamine in MeOH. Reduction of oxime (IV) to the benzylic amine (V) is carried out by catalytic hydrogenation in the presence of Raney nickel. Subsequent reductive alkylation of amine (V) with 4-t-butylbenzaldehyde (VI) furnishes the secondary amine (VII). This is then acylated by pyridine-3-sulfonyl chloride (VIII) producing sulfonamide (IX). The t-butyl ester group of (IX) is finally cleaved with trifluoroacetic acid to give the corresponding carboxylic acid.
【1】 Rosati, R.L.; Lefker, B.A.; Cameron, K.O. (Pfizer Inc.); Prostaglandin agonists and their use to treat bone disorders. EP 1021410; JP 2001519414; US 6498172; WO 9919300 . |
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) | 28537 | 3-hydroxybenzaldehyde | 100-83-4 | C7H6O2 | 详情 | 详情 |
(II) | 17430 | 2-Bromoacetic acid tert-butyl ester; tert-butyl 2-bromoacetate; tert-Butyl bromoacetate | 5292-43-3 | C6H11BrO2 | 详情 | 详情 |
(III) | 64442 | tert-butyl 2-(3-formylphenoxy)acetate | C13H16O4 | 详情 | 详情 | |
(IV) | 64443 | tert-butyl 2-{3-[(hydroxyimino)methyl]phenoxy}acetate | C13H17NO4 | 详情 | 详情 | |
(V) | 64444 | tert-butyl 2-[3-(aminomethyl)phenoxy]acetate | C13H19NO3 | 详情 | 详情 | |
(VI) | 16638 | 4-(tert-butyl)benzaldehyde; 4-tert-Butyl-benzaldehyde | 939-97-9 | C11H14O | 详情 | 详情 |
(VII) | 64445 | tert-butyl 2-[3-({[4-(tert-butyl)benzyl]amino}methyl)phenoxy]acetate | C24H33NO3 | 详情 | 详情 | |
(VIII) | 64446 | 3-pyridinesulfonyl chloride | C5H4ClNO2S | 详情 | 详情 | |
(IX) | 64447 | tert-butyl 2-(3-{[[4-(tert-butyl)benzyl](3-pyridinylsulfonyl)amino]methyl}phenoxy)acetate | C29H36N2O5S | 详情 | 详情 |