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3'-氨基-[1,1'-联苯]-3-羧酸甲酯 → (R)-3'-[[2-[[2-(3-Chlorophenyl)-2-[[(tert-butyl)dimethylsilyl]oxy]ethyl][(tert-butoxy)carbonyl]amino]ethyl]amino]-[1,1'-biphenyl]-3-carboxylic acid methyl ester

HRID 1069094
笔记
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反应方程式

HRID 1069094 反应方程式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4].[C:18]([O:22][C:23]([N:25]([CH2:43][CH:44]=O)[CH2:26][C@H:27]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=1)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][CH2:44][CH2:43][N:25]([CH2:26][C@@H:27]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=3)[O:35][Si:36]([C:39]([CH3:40])([CH3:41])[CH3:42])([CH3:38])[CH3:37])[C:23]([O:22][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:24])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4]
参与物实验过程后处理来源与证据反应笔记

参与物

6

反应物 3

HCID 13942153'-氨基-[1,1'-联苯]-3-羧酸甲酯HCID 5049666三乙酰氧基硼氢化钠HCID 20666899(R)-[(tert-butoxycarbonyl)-[2-(tertbutyidimethylsilanyloxy)-2-(3-chlorophenyl)ethyl]amino}acetaldehyde

产物 1

HCID 11592646(R)-3'-[[2-[[2-(3-Chlorophenyl)-2-[[(tert-butyl)dimethylsilyl]oxy]ethyl][(tert-butoxy)carbonyl]amino]ethyl]amino]-[1,1'-biphenyl]-3-carboxylic acid methyl ester收率 66.6%

试剂、催化剂与溶剂 2

HCID 176醋酸催化剂
HCID 6344二氯甲烷溶剂

实验过程

To a stirred solution of 3′-amino-[1,1′-biphenyl]-3-carboxylic acid methyl ester (3.0 g) and (R)-[(tert-butoxycarbonyl)-[2-(tertbutyidimethylsilanyloxy)-2-(3-chlorophenyl)ethyl]amino}acetaldehyde (8.2 g) in anhydrous dichloromethane (65 mL) was added acetic acid (8 drops). After stirring for twenty-five minutes, sodium triacetoxyborohydride (5.6 g) was added and the reaction stirred overnight. The reaction was quenched with saturated aqueous sodium bicarbonate and more dichloromethane was added. The organic layer was dried over sodium sulfate and the solvent was removed under reduced pressure to yield a white foam. The residue was purified by silica gel chromatography and eluted with 9:1 hexane:ethyl acetate to provide the title compound as a white foam (5.62 g).

后处理

  1. stirringthe reaction stirred overnight
  2. customThe reaction was quenched with saturated aqueous sodium bicarbonate and more dichloromethane
  3. additionwas added
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customto yield a white foam
  7. customThe residue was purified by silica gel chromatography
  8. washeluted with 9:1 hexane

来源与证据

ORD记录
ord-89c516ae0e5c435ebf42aa419104312b
来源数据集
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
专利号
US06251925B1

反应笔记

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本页导航参与物实验过程后处理来源与证据反应笔记