Hydrochloric Acid → cis4-hydroxy-N-benzyloxycarbonyl-D-proline 2-oxo-1,2-diphenylethyl ester

HRID 431755Notes

Reaction equation

HRID 431755 reaction equation
[O:1]=[C:2]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH:3]([O:10][C:11](=[O:35])[C@H:12]1[CH2:16][C@@H:15]([O:17][Si](C(C)(C)C)(C)C)[CH2:14][N:13]1[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.C([O-])(O)=O.[Na+]>CO.C1COCC1>[O:1]=[C:2]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH:3]([O:10][C:11](=[O:35])[C@H:12]1[CH2:16][C@@H:15]([OH:17])[CH2:14][N:13]1[C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 69996365cis4-(tert-butyldimethylsilyloxy)-N-benzyloxycarbonyl-D-proline 2-oxo-1,2-diphenylethyl ester

Product 1

HCID 69994676cis4-hydroxy-N-benzyloxycarbonyl-D-proline 2-oxo-1,2-diphenylethyl esterYield 80.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of cis-4-(tert-butyldimethylsilyloxy)-N-benzyloxycarbonyl-D-proline 2-oxo-1,2-diphenylethyl ester (21.62 g) in MeOH-THF (2:1, 380 mL) was added 1N HCl (76 mL) at 5° C., and the mixture was stirred at room temperature for 24 hours. To the reaction mixture was added NaHCO3 (6.7 g) at 5° C. The organic solvent was evaporated, and the residue was extracted with EtOAc. The organic layer was washed with water and brine, dried (MgSO4), and evaporated in vacuo. The residue was purified by silica gal column chromatography (hexane-EtOAc, 2:1˜1:3 elution) to give cis4-hydroxy-N-benzyloxycarbonyl-D-proline 2-oxo-1,2-diphenylethyl ester (13.90 g).

Workup

  1. customThe organic solvent was evaporated
  2. extractionthe residue was extracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gal column chromatography (hexane-EtOAc, 2:1˜1:3 elution)

Sources & evidence

ORD record
ord-1083dd90e6ab4d97946432f0129e1205
Source dataset
uspto-grants-2003_12
Patent number
US06660759B1

Reaction notes

Loading…