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【结 构 式】 
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【分子编号】22715 【品名】benzhydryl 4-bromo-3-oxobutanoate 【CA登记号】 |
【 分 子 式 】C17H15BrO3 【 分 子 量 】347.2083 【元素组成】C 58.81% H 4.35% Br 23.01% O 13.82% |
合成路线1
该中间体在本合成路线中的序号：(XIV)Synthesis of intermediate (I): 1c) The bromination of diketene (XIII) followed by reaction with diphenylmethanol gives diphenylmethyl 4-bromoacetoacetate (XIV), which by cyclization with thiourea by means of K2CO3 yields diphenylmethyl 2-(2-aminothiazol-4-yl)acetate (XV). The reaction of (XV) with benzyloxycarbonyl chloride and pyridine affords the protected compound (XVI), which is formylated with diphenyl methyl formiate (XVII) and NaH to afford diphenyl methyl 2-(2-benzyloxycarbonylamino)thiazol-4-yl-3-hydroxyacrylate (XVIII) The Wittig condensation of (XVIII) with benzyl triphenylphosphoranylidene acetate (XIX) gives diphenylmethyl 2-[2-(benzyloxycarbonylamino)thiazol-4-yl]-4-(benzyloxycarbonyl)-2-butenoate (XX), which is selectively hydrolyzed with trifluoroacetic acid and anisole lo acid.
| 【1】 Yoshioka, M.; Synthetic studies related to oral beta-lactam antibiotics. Pure Appl Chem 1987, 59, 8, 1041. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 | |
| (I) | 22689 | (Z)-5-(benzyloxy)-2-(2-[[(benzyloxy)carbonyl]amino]-1,3-thiazol-4-yl)-5-oxo-2-pentenoic acid | C23H20N2O6S | 详情 | 详情 | |
| (XIII) | 11367 | 4-Methylene-2-oxetanone; Acetyl ketene | 674-82-8 | C4H4O2 | 详情 | 详情 |
| (XIV) | 22715 | benzhydryl 4-bromo-3-oxobutanoate | C17H15BrO3 | 详情 | 详情 | |
| (XV) | 22716 | benzhydryl 2-amino-1,3-thiazole-4-carboxylate | C17H14N2O2S | 详情 | 详情 | |
| (XVI) | 22717 | benzhydryl 2-[[(benzyloxy)carbonyl]amino]-1,3-thiazole-4-carboxylate | C25H20N2O4S | 详情 | 详情 | |
| (XVII) | 22718 | benzhydryl formate | C14H12O2 | 详情 | 详情 | |
| (XVIII) | 22719 | benzhydryl (Z)-2-(2-[[(benzyloxy)carbonyl]amino]-1,3-thiazol-4-yl)-3-hydroxy-2-propenoate | C27H22N2O5S | 详情 | 详情 | |
| (XIX) | 22668 | benzyl 2-(triphenylphosphoranylidene)acetate | C27H23O2P | 详情 | 详情 | |
| (XX) | 22721 | 1-benzhydryl 5-benzyl (Z)-2-(2-[[(benzyloxy)carbonyl]amino]-1,3-thiazol-4-yl)-2-pentenedioate | C36H30N2O6S | 详情 | 详情 |