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

HRID 431754Notes

Reaction equation

HRID 431754 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-6104a5f96b474949858929283c9c071e
Source dataset
uspto-grants-2003_12
Patent number
US06660759B1

Reaction notes

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