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(1,1'-Biphenyl)-3-carboxylic acid, 3'-amino-, methyl ester → (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
ノート
印刷プレビュー

反応式

HRID 1069094 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 1394215(1,1'-Biphenyl)-3-carboxylic acid, 3'-amino-, methyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 20666899(R)-[(tert-butoxycarbonyl)-[2-(tertbutyidimethylsilanyloxy)-2-(3-chlorophenyl)ethyl]amino}acetaldehyde

生成物 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収率 66.6%

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-89c516ae0e5c435ebf42aa419104312b
出典データセット
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06251925B1

反応ノート

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