N-[1-ethoxycarbonyl-5,5-ethylenedioxy-5-(2-thienyl)pentyl]-L-alanyl-L-proline t-butyl ester → HCID 70483395, compound

HRID 370841Notes

Reaction equation

HRID 370841 reaction equation
[C:1]([O:5][C:6](=[O:36])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:35])[C@H:13]([CH3:34])[NH:14][CH:15]([C:29]([O:31]CC)=[O:30])[CH2:16][CH2:17][CH2:18][C:19]1([O:28][CH2:27][CH2:26][O:25]1)[C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)C>[C:1]([O:5][C:6](=[O:36])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:35])[C@H:13]([CH3:34])[NH:14][CH:15]([C:29]([OH:31])=[O:30])[CH2:16][CH2:17][CH2:18][C:19]1([O:25][CH2:26][CH2:27][O:28]1)[C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 1

HCID 54094537N-[1-ethoxycarbonyl-5,5-ethylenedioxy-5-(2-thienyl)pentyl]-L-alanyl-L-proline t-butyl ester

Product 1

HCID 70483395HCID 70483395, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aqueous N-sodium hydroxide solution (2.5 ml.) was added to a solution of N-[1-ethoxycarbonyl-5,5-ethylenedioxy-5-(2-thienyl)pentyl]-L-alanyl-L-proline t-butyl ester (Example 17; 1.2 g.) in ethanol (7.5 ml.) and the mixture was stirred at laboratory temperature for 24 hours and the ethanol was then removed by evaporation under reduced pressure. Water (10 ml.) was added, the solution was washed with dichloromethane and then acidified to pH 5 with aqueous 2N hydrochloric acid, and the mixture was filtered. There was thus obtained as solid residue Isomer A of N-[1-carboxy-5,5-ethylenedioxy-5-(2-thienyl)pentyl]-L-alanyl-L-proline t-butyl ester.

Workup

  1. customthe ethanol was then removed by evaporation under reduced pressure
  2. additionWater (10 ml.) was added
  3. washthe solution was washed with dichloromethane
  4. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-e3c257d048d24a7292eabee722f12076
Source dataset
uspto-grants-1985_07
Patent number
US04528282

Reaction notes

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