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

HRID 370844

Reaktionsgleichung

Reaktionsgleichung von HRID 370844
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1d6fdac4744840cfb5dd1e2285f22cac
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04528282

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