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【结 构 式】 
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【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% |
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 |