Ethylmorpholine → (S)-1-(tert-Butyl)pyrrolidine-2-carboxamide

HRID 267137

Reaktionsgleichung

Reaktionsgleichung von HRID 267137
N#N.N[C@@H](CC1C=CC=CC=1)[C@H](O)C[C@@:7]1([C:16]([NH2:18])=[O:17])[CH2:11][CH2:10][CH2:9][N:8]1[C:12]([CH3:15])([CH3:14])[CH3:13].C(OC(N[C@H](C(O)=O)CSC)=O)C1C=CC=CC=1.OC1C2N=NNC=2C=CC=1.C(N1CCOCC1)C.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.C(OCC)(=O)C>[C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:16]([NH2:18])=[O:17])([CH3:15])([CH3:13])[CH3:14]

Komponenten

8

Edukt 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 57121652N-((Benzyloxy)carbonyl)-S-methyl-L-cysteineHCID 86746262N2 [3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1 tert.butyl-L-prolinamideHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 54424267(S)-1-(tert-Butyl)pyrrolidine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 650 mg of N2 -[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide and 538 mg of N-(benzyloxycarbonyl)-S-methyl-L-cysteine in 20 ml of dry tetrahydrofuran was cooled in an ice/salt mixture. 270 mg of hydroxybenzotriazole, 230 mg of N-ethylmorpholine and 412 mg of dicyclohexylcarbodiimide were added and the mixture was stirred for 16 hours. The mixture was diluted with ethyl acetate and filtered. The filtrate was washed with aqueous sodium bicarbonate solution and sodium chloride solution. The solvent was removed by evaporation and the residue was chromatographed on silica gel using System G for the elution to give 800 mg of N2 -[3(S)-[N-(benzyloxycarbonyl)-S-methyl-L-cysteinyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide; MS: m/e 585 [M+H]+.

Aufarbeitung

  1. filtrationfiltered
  2. washThe filtrate was washed with aqueous sodium bicarbonate solution and sodium chloride solution
  3. customThe solvent was removed by evaporation
  4. customthe residue was chromatographed on silica gel using System G for the elution

Quellen und Nachweise

ORD-Eintrag
ord-742ac0a6f4fd42f69e868d2dcf1f5dc7
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05652369

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