N-[1,1-dimethoxycarbonyl-4-oxo-4-(2-thienyl)butyl]-L-alanyl-L-proline t-butyl ester → N-[1-methoxycarbonyl-4-oxo-4-(2-thienyl)butyl]-L-alanyl-L-proline t-butyl ester

HRID 370846

Reaction equation

HRID 370846 reaction equation
[C:1]([O:5][C:6](=[O:35])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:34])[C@H:13]([CH3:33])[NH:14][C:15](C(OC)=O)([C:25]([O:27][CH3:28])=[O:26])[CH2:16][CH2:17][C:18](=[O:24])[C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)([CH3:4])([CH3:3])[CH3:2]>CO.O>[C:1]([O:5][C:6](=[O:35])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:34])[C@H:13]([CH3:33])[NH:14][CH:15]([C:25]([O:27][CH3:28])=[O:26])[CH2:16][CH2:17][C:18](=[O:24])[C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 1

HCID 70443263N-[1,1-dimethoxycarbonyl-4-oxo-4-(2-thienyl)butyl]-L-alanyl-L-proline t-butyl ester

Product 1

HCID 70484536N-[1-methoxycarbonyl-4-oxo-4-(2-thienyl)butyl]-L-alanyl-L-proline t-butyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Aqueous N-sodium hydroxide solution (6.2 ml.) was added to a solution of N-[1,1-dimethoxycarbonyl-4-oxo-4-(2-thienyl)butyl]-L-alanyl-L-proline t-butyl ester (Example 31; 3.0 g.) in a mixture of methanol (3 ml.) and water (1.5 ml.) and the mixture was stirred at laboratory temperature for 16 hours and then evaporated to dryness under reduced pressure. The mixture was partitioned between water and ethyl acetate and the aqueous layer was separated, acidified to pH 5 with aqueous N-hydrochloric acid and extracted with dichloromethane. The extract was dried over magnesium sulphate and evaporated to dryness. There was thus obtained as residual oil N-[1-methoxycarbonyl-4-oxo-4-(2-thienyl)butyl]-L-alanyl-L-proline t-butyl ester.

Workup

  1. customevaporated to dryness under reduced pressure
  2. customThe mixture was partitioned between water and ethyl acetate
  3. customthe aqueous layer was separated
  4. extractionextracted with dichloromethane
  5. dry with materialThe extract was dried over magnesium sulphate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-0d72e48250804d1f9118cef71c806eb6
Source dataset
uspto-grants-1985_07
Patent number
US04528282

Linked notes

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