Quinaldic Acid → N-tert.butyl-1-[2(R)-hydroxy-4-phenyl-3(S)-[[N-(2-quinolylcarbonyl)-L-cysteinyl]amino]butyl]-2(S)-piperidinecarboxamide

HRID 267164

Reaktionsgleichung

Reaktionsgleichung von HRID 267164
[C:1]([NH:5][C:6]([C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[CH2:14][C@@H:15]([OH:31])[C@@H:16]([NH:24][C:25](=[O:30])[C@H:26]([CH2:28][SH:29])[NH2:27])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:32](O)(=[O:43])[C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=1.OC1C2N=NNC=2C=CC=1.C(N1CCOCC1)C.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[C:1]([NH:5][C:6]([C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[CH2:14][C@@H:15]([OH:31])[C@@H:16]([NH:24][C:25](=[O:30])[C@H:26]([CH2:28][SH:29])[NH:27][C:32]([C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=1)=[O:43])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 5

HCID 7124Quinaldic AcidHCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 86746294N-tert.butyl-1-[3(S)-[(L-cysteinyl)amino]-2(R)-hydroxy-4-phenylbutyl]-2(S)-piperidinecarboxamideHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 86746293N-tert.butyl-1-[2(R)-hydroxy-4-phenyl-3(S)-[[N-(2-quinolylcarbonyl)-L-cysteinyl]amino]butyl]-2(S)-piperidinecarboxamideAusbeute 41,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 650 mg of N-tert.butyl-1-[3(S)-[(L-cysteinyl)amino]-2(R)-hydroxy-4-phenylbutyl]-2(S)-piperidinecarboxamide and 242 mg of quinaldic acid was cooled in an ice/salt mixture. 189 mg of hydroxybenzotriazole, 161 mg of N-ethylmorpholine and 317 mg of dicyclohexylcarbodiimide were added and the mixture was stirred for 64 hours. The mixture was diluted with ethyl acetate and filtered, and the filtrate was then evaporated. The residue was partitioned between dichloromethane and aqueous sodium bicarbonate solution. The organic phase was washed with sodium chloride solution and then evaporated. The residue was chromatographed on silica gel using dichloromethane/methanol (19:1) for the elution to give 350 mg of N-tert.butyl-1-[2(R)-hydroxy-4-phenyl-3(S)-[[N-(2-quinolylcarbonyl)-L-cysteinyl]amino]butyl]-2(S)-piperidinecarboxamide as a white solid; MS: m/e 620 [M+H]+.

Aufarbeitung

  1. filtrationfiltered
  2. customthe filtrate was then evaporated
  3. customThe residue was partitioned between dichloromethane and aqueous sodium bicarbonate solution
  4. washThe organic phase was washed with sodium chloride solution
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washfor the elution

Quellen und Nachweise

ORD-Eintrag
ord-38a760da742447fd83919f396b336eec
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05652369

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