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【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%

与该中间体有关的原料药合成路线共 1 条

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
Extended Information