• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】13599

【品名】4-[(2,2-Dimethylpropanoyl)oxy]benzenesulfonic acid

【CA登记号】

【 分 子 式 】C11H14O5S

【 分 子 量 】258.29516

【元素组成】C 51.15% H 5.46% O 30.97% S 12.41%

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:(VI)

The condensation of 4-(pivaloyloxy)benzenesulfonyl chloride (I) with the glycine benzyl ester (II) in pyridine gives N-[2-[4-(pivaloyloxy)phenylsulfonamido]benzoyl]glycine benzyl ester (III), which is then debenzylated by hydrogenolysis with H2 over Pd/C in methanol. The starting compounds (I) and (II) are obtained as follows: 1) The condensation of pivaloyl chloride (IV) with 4-hydroxybenzenesulfonic acid (V) by means of NaOH in THF - water gives 4-(pivaloyloxy)benzenesulfonic acid (VI), which is then treated with SOCl2 to afford the corresponding acyl chloride (I). 2) The condensation of 2-nitrobenzoyl chloride (VII) with glycine benzyl ester (VIII) by means of triethylamine in dichloromethane gives N-(2-nitrobenzoyl)glycine benzyl ester (IX), which is then reduced with Fe - HCl in THF - water to the amino derivative (II).

1 Imaki, K.; Arai, Y.; Okegawa, T. (Ono Pharmaceutical Co., Ltd.); Derivs. of p-substituted phenyl ester of pivalic acid. EP 0347168; JP 1991020253; JP 1994179645; US 5017610; US 5336681; US 5403850 .
2 Imaki, K.; Wakatsuka, H. (Ono Pharmaceutical Co., Ltd.); Glycine deriv. monosodium salt tetrahydrate having an inhibitory effect on elastase. EP 0539223; JP 1993194366 .
3 Castaner, J.; Graul, A.; Prous, J.; Ono-5046. Drugs Fut 1994, 19, 11, 1000.
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) 13594 4-(chlorosulfonyl)phenyl pivalate C11H13ClO4S 详情 详情
(II) 13595 benzyl 2-[(2-aminobenzoyl)amino]acetate C16H16N2O3 详情 详情
(III) 13596 4-[[2-([[2-(benzyloxy)-2-oxoethyl]amino]carbonyl)anilino]sulfonyl]phenyl pivalate C27H28N2O7S 详情 详情
(IV) 13597 2,2-Dimethylpropanoyl chloride; Pivaloyl chloride 3282-30-2 C5H9ClO 详情 详情
(V) 13598 4-Hydroxybenzenesulfonic acid; p-Phenolsulfonic acid 98-67-9 C6H6O4S 详情 详情
(VI) 13599 4-[(2,2-Dimethylpropanoyl)oxy]benzenesulfonic acid C11H14O5S 详情 详情
(VII) 21099 o-nitrobenzoyl chloride; 2-nitrobenzoyl chloride 610-14-0 C7H4ClNO3 详情 详情
(VIII) 13601 benzyl 2-aminoacetate; Glycine benzyl ester hydrochloride 1738-68-7 C9H11NO2 详情 详情
(IX) 13602 benzyl 2-[(2-nitrobenzoyl)amino]acetate C16H14N2O5 详情 详情
Extended Information