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

HRID 466867Notes

Reaction equation

HRID 466867 reaction equation
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]

Participants

8

Reactant 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, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-9f1d0ee3df554ae7b390e6689f635dd7
Source dataset
uspto-grants-1992_10
Patent number
US05157041

Reaction notes

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