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

HRID 370844

Reaction equation

HRID 370844 reaction equation
[C:1]([O:5][C:6](=[O:26])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:25])[C@H:13]([CH3:24])[NH:14][CH:15]([C:20]([O:22][CH3:23])=[O:21])[C:16]([O:18][CH3:19])=[O:17])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)[CH2:30][CH2:31][C:32]([C:34]1[S:35][CH:36]=[CH:37][CH:38]=1)=[O:33].C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([O:5][C:6](=[O:26])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:25])[C@H:13]([CH3:24])[NH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])([C:20]([O:22][CH3:23])=[O:21])[CH2:30][CH2:31][C:32](=[O:33])[C:34]1[S:35][CH:36]=[CH:37][CH:38]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 28768913-(Dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochlorideHCID 18598656N-(dimethoxycarbonylmethyl)-L-alanyl-L-proline t-butyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A-mixture of N-(dimethoxycarbonylmethyl)-L-alanyl-L-proline t-butyl ester (2.0 g.), 3-dimethylamino-1-(2-thienyl)propan-1-one hydrochloride (1.8 g.), potassium carbonate (2.0 g.) and methanol (15 ml.) was stirred at laboratory temperature for 16 hours and then evaporated to dryness under reduced pressure. The residue was stirred with dichloromethane, the mixture was filtered through a filter-aid and the filtrate was evaporated to dryness under reduced pressure. The residue was purified by chromatography on a silica gel column using a 19:1 v/v mixture of dichloromethane and ethyl acetate as eluant. There was thus obtained as an oil N-[1,1-dimethoxycarbonyl-4-oxo-4-(2-thienyl)butyl]-L-alanyl-L-proline t-butyl ester.

Workup

  1. customevaporated to dryness under reduced pressure
  2. filtrationthe mixture was filtered through
  3. filtrationa filter-aid
  4. customthe filtrate was evaporated to dryness under reduced pressure
  5. customThe residue was purified by chromatography on a silica gel column
  6. additiona 19:1 v/v mixture of dichloromethane and ethyl acetate as eluant

Sources & evidence

ORD record
ord-1d6fdac4744840cfb5dd1e2285f22cac
Source dataset
uspto-grants-1985_07
Patent number
US04528282

Linked notes

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