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【结 构 式】 
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【分子编号】27848 【品名】tert-butyl 2-(4-acetylanilino)-2-oxoethyl(benzyl)carbamate 【CA登记号】 |
【 分 子 式 】C22H26N2O4 【 分 子 量 】382.45952 【元素组成】C 69.09% H 6.85% N 7.32% O 16.73% |
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：(V)The N-alkylation of N-(tert-butoxycarbonyl)glycine (I) with benzyl bromide (II) by means of NaH in THF gives N-benzyl-N-(tert-butoxycarbonyl)glycine (III), which is condensed with 4-aminoacetophenone (IV) by means of isobutyl chloroformate and TEA in dichloromethane yielding the corresponding glycinamide (V). The cyclization of (V) with thiourea (VI) by means of I2 in refluxing isopropanol affords, after work up, the N-benzyl-glycinamide (VII), which is finally acylated with pyridine-4-carbonyl chloride by means of TEA and DMAP in dichloromethane.
| 【1】 Hargrave, K.D.; Simoneau, B.; Faucher, A.-M.; Thavonekham, B.; Grygon, C.A.; Crute, J.J. (Boehringer Ingelheim (Canada) Ltd.; Boehringer Ingelheim Pharmaceuticals Inc.); Phenyl thiazole derivs. with anti-herpes virus properties. EP 0871619; JP 2000502702; US 6057451; WO 9724343 . |
| 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) | 18066 | N-alpha-t-BOC-glycine; 2-[(tert-butoxycarbonyl)amino]acetic acid | 4530-20-5 | C7H13NO4 | 详情 | 详情 |
| (II) | 12912 | 1-(Bromomethyl)benzene; Alpha-bromotoluene | 100-39-0 | C7H7Br | 详情 | 详情 |
| (III) | 27846 | 2-[benzyl(tert-butoxycarbonyl)amino]acetic acid | C14H19NO4 | 详情 | 详情 | |
| (IV) | 27847 | 1-(4-aminophenyl)-1-ethanone | 99-92-3 | C8H9NO | 详情 | 详情 |
| (V) | 27848 | tert-butyl 2-(4-acetylanilino)-2-oxoethyl(benzyl)carbamate | C22H26N2O4 | 详情 | 详情 | |
| (VI) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
| (VII) | 27849 | N-[4-(2-amino-1,3-thiazol-4-yl)phenyl]-2-(benzylamino)acetamide | C18H18N4OS | 详情 | 详情 | |
| (VIII) | 27850 | isonicotinoyl chloride | 39178-35-3 | C6H4ClNO | 详情 | 详情 |
Extended Information