Sodium Hydroxide → HCID 131719465, compound

HRID 1735410Notes

Reaction equation

HRID 1735410 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:28])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:27])[C@@H:12]1[CH2:16][S:15][CH2:14][N:13]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>CO>[CH2:20]([O:19][C:17]([N:13]1[CH2:14][S:15][CH2:16][C@H:12]1[C:11]([N:7]1[CH2:8][CH2:9][CH2:10][C@H:6]1[C:5]([OH:28])=[O:4])=[O:27])=[O:18])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53917790HCID 53917790, compound

Product 1

HCID 131719465HCID 131719465, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1N Sodium hydroxide (45 ml) was dropwise added to a methanol solution (120 ml) of N-(benzyloxycarbonyl)-L-thioprolyl-L-proline methyl ester (11.84 g) under ice-cooling, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated and the residue was dissolved in water. The aqueous solution was acidified with concentrated hydrochloric acid under ice-cooling and extracted with chloroform. The extract was washed with water and concentrated to give the title compound (6.47 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in water
  4. temperaturecooling
  5. extractionextracted with chloroform
  6. washThe extract was washed with water
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-29ecb8b9e2864fc8b538affa506f1927
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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