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

HRID 54090Notes

Reaction equation

HRID 54090 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-ad973eb644d44f46a9641b14118382e9
Source dataset
uspto-grants-1997_04
Patent number
US05620987

Reaction notes

Loading…