Dicyclohexylcarbodiimide → N-(3-acetylthio-2-trifluoromethylpropanoyl)-L-proline tertbutyl ester

HRID 2309042Notes

Reaction equation

HRID 2309042 reaction equation
[C:1]([O:5][C:6](=[O:12])[C@@H:7]1[CH2:11][CH2:10][CH2:9][NH:8]1)([CH3:4])([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[C:28]([S:31][CH2:32][CH:33]([C:37]([F:40])([F:39])[F:38])[C:34](O)=[O:35])(=[O:30])[CH3:29]>ClCCl>[C:1]([O:5][C:6](=[O:12])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:34](=[O:35])[CH:33]([C:37]([F:38])([F:39])[F:40])[CH2:32][S:31][C:28](=[O:30])[CH3:29])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 6453108L-Proline 1,1-dimethylethyl esterHCID 128330143-Acetylthio-2-trifluoromethylpropanoic acid

Product 1

HCID 54253056N-(3-acetylthio-2-trifluoromethylpropanoyl)-L-proline tertbutyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

L-proline tert-butyl ester (5.1 g.) is dissolved in dichloromethane (40 ml.) and the solution is stirred and chilled in an ice bath. Dicyclohexylcarbodiimide (6.2 g.) dissolved in dichloromethane (15 ml.) is added followed immediately by a solution of 3-acetylthio-2-trifluoromethylpropanoic acid (6.5 g.) in dichloromethane (5 ml.). After fifteen minutes stirring in the ice bath and sixteen hours at room temperature, the precipitate formed is filtered off and the filtrate is concentrated to dryness in vacuo. The residue is dissolved in ethyl acetate and washed neutral. The organic phase is dried over magnesium sulfate and concentrated to dryness in vacuo to give N-(3-acetylthio-2-trifluoromethylpropanoyl)-L-proline tert-butyl ester.

Workup

  1. temperaturechilled in an ice bath
  2. additionis added
  3. customthe precipitate formed
  4. filtrationis filtered off
  5. concentrationthe filtrate is concentrated to dryness in vacuo
  6. dissolutionThe residue is dissolved in ethyl acetate
  7. washwashed neutral
  8. dry with materialThe organic phase is dried over magnesium sulfate
  9. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-66380974cfcf41569ef202f9018611a4
Source dataset
uspto-grants-1987_09
Patent number
US04692458

Reaction notes

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