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【结 构 式】 
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【分子编号】31692 【品名】N-formyl-2-(4-benzyloxyphenyl)glycine; (2R)-2-[4-(benzyloxy)phenyl]-2-(formylamino)ethanoic acid 【CA登记号】 |
【 分 子 式 】C16H15NO4 【 分 子 量 】285.29944 【元素组成】C 67.36% H 5.3% N 4.91% O 22.43% |
合成路线1
该中间体在本合成路线中的序号：(XI)The formylation of 2-(4-hydroxyphenyl)glycine (IX) as usual gives N-formyl-2-(4-hydroxyphenyl)glycine (X), which by treatment with benzyl alcohol as before yields N-formyl-2-(4-benzyloxyphenyl)glycine (XI). The condensation of (XI) with the amine (IV) by means of butyl chloroformate affords the corresponding amide (XII), which is deformylated by treatment with HCl in methanol to give the glycinamide (XIII). The diazotation of (XIII) with NaNO2 in acetic acid affords N-(3,4-dimethoxyphenylethyl)-O-acetyl-4-benzyloxymandel-amide (XIV), which is finally reduced and deacetylated with LiAlH4 in THF yielding the protected product (VI).
| 【1】 Noguchi, K.; Irie, K.; Preparation of optically active benzyl alcohol derivative. JP 54070232 . |
| 【2】 Noguchi, K.; Irie, K.; Preparation of optically active benzyl alcohol derivative. JP 54070233 . |
| 【3】 Blancafort, P.; Castaner, J.; Serradell, M.N.; TA-064. Drugs Fut 1982, 7, 6, 407. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 10098 | 2-(3,4-Dimethoxyphenyl)-1-ethanamine; 3,4-Dimethoxyphenethylamine; 2-(3,4-Dimethoxyphenyl)ethylamine | 120-20-7 | C10H15NO2 | 详情 | 详情 |
| (VI) | 31687 | (1R)-1-[4-(benzyloxy)phenyl]-2-[(3,4-dimethoxyphenethyl)amino]-1-ethanol | C25H29NO4 | 详情 | 详情 | |
| (IX) | 31690 | (2R)-2-amino-2-(4-hydroxyphenyl)ethanoic acid; (2R)-2-(4-hydroxyphenyl)glycine; D-(-)-p-Hydroxyphenylglycine; (R)-2-amino-2-(4-hydroxyphenyl)acetic acid | 22818-40-2 | C8H9NO3 | 详情 | 详情 |
| (X) | 31691 | (2R)-2-(formylamino)-2-(4-hydroxyphenyl)ethanoic acid | C9H9NO4 | 详情 | 详情 | |
| (XI) | 31692 | N-formyl-2-(4-benzyloxyphenyl)glycine; (2R)-2-[4-(benzyloxy)phenyl]-2-(formylamino)ethanoic acid | C16H15NO4 | 详情 | 详情 | |
| (XII) | 31693 | (2R)-2-[4-(benzyloxy)phenyl]-N-(3,4-dimethoxyphenethyl)-2-(formylamino)ethanamide | C26H28N2O5 | 详情 | 详情 | |
| (XIII) | 31694 | (2R)-2-amino-2-[4-(benzyloxy)phenyl]-N-(3,4-dimethoxyphenethyl)ethanamide | C25H28N2O4 | 详情 | 详情 | |
| (XIV) | 31695 | (1R)-1-[4-(Benzyloxy)phenyl]-2-[(3,4-dimethoxyphenethyl)amino]-2-oxoethyl acetate; N-(3,4-Dimethoxyphenylethyl)-O-acetyl-4-benzyloxymandel-amide | C27H29NO6 | 详情 | 详情 |