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

HRID 1733335Notes

Reaction equation

HRID 1733335 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 mg.) and the solution is stirred and chilled in an ice bath. Dicyclohexylcarbodiimide (6.q 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 1-(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-2a94d482f2a74bb6888609a787a83a0f
Source dataset
uspto-grants-1980_12
Patent number
US04241076

Reaction notes

Loading…