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

HRID 1757750Notes

Reaction equation

HRID 1757750 reaction equation
N#N.N[C@@H](CC1C=CC=CC=1)[C@H](O)CN1CCC[C@H]1C(N[C:12]([CH3:15])([CH3:14])[CH3:13])=O.C([O:34]C(N[C@H](C(O)=O)CSC)=O)C1C=CC=CC=1.OC1[C:54]2[N:53]=N[NH:51][C:50]=2[CH:49]=[CH:48][CH:47]=1.C(N1CCOCC1)C.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.C(OCC)(=O)C>[C:12]([N:51]1[CH2:47][CH2:48][CH2:49][C@H:50]1[C:54]([NH2:53])=[O:34])([CH3:15])([CH3:14])[CH3:13]

Participants

8

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 57121652N-((Benzyloxy)carbonyl)-S-methyl-L-cysteineHCID 131719114HCID 131719114, compoundHCID 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]-N -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 andthe 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 removedby 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. customevaporation
  4. customthe residue was chromatographed on silica gel using System G for the elution

Sources & evidence

ORD record
ord-78180dea416a4e24b05d22998ba93eb6
Source dataset
uspto-grants-1995_08
Patent number
US05446161

Reaction notes

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