Benzoin → cis4-(tert-butyldimethylsilyloxy)-N-benzyloxycarbonyl-D-proline 2-oxo-1,2-diphenylethyl ester

HRID 431754노트

반응식

HRID 431754 반응식
[Si:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[C@@H:11]([C:24]([OH:26])=[O:25])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:27]1([C:33]([CH:35]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)O)=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[O:34]=[C:33]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH:35]([O:25][C:24](=[O:26])[C@H:11]1[CH2:10][C@@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:13][N:12]1[C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

참가 물질

6

반응물 3

HCID 8400BenzoinHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69995641cis4-(tert-butyldimethylsilyloxy)-N-benzyloxycarbonyl-D-proline

생성물 1

HCID 69996365cis4-(tert-butyldimethylsilyloxy)-N-benzyloxycarbonyl-D-proline 2-oxo-1,2-diphenylethyl ester수율 65.4%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a mixture of cis4-(tert-butyldimethylsilyloxy)-N-benzyloxycarbonyl-D-proline (21.87 g), benzoin (12.25 g), and 4-dimethylaminopyridine (7.04 g) in CH2Cl2 (200 mL) was added 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (10.52 mL) at 5° C., and the mixture was stirred at room temperature for 20 hours. The reaction mixture was evaporated, and the residue was dissolved in EtOAc (250 mL), washed with 1N HCl (150 mL), water, saturated sodium hydrogen carbonate solution, water and brine, dried (MgSO4), and evaporated in vacuo. The residue was purified by silica gal column chromatography (hexane-EtOAc, 5:2 elution) to give cis4-(tert-butyldimethylsilyloxy)-N-benzyloxycarbonyl-D-proline 2-oxo-1,2-diphenylethyl ester (21.62 g).

후처리

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue was dissolved in EtOAc (250 mL)
  3. washwashed with 1N HCl (150 mL), water, saturated sodium hydrogen carbonate solution, water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gal column chromatography (hexane-EtOAc, 5:2 elution)

출처 및 근거

ORD 기록
ord-6104a5f96b474949858929283c9c071e
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660759B1

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