HCID 53991841, compound → (R)-1-[[4-[2-[(R)-2-carboxy-4,4-difluoropyrrolidin-1-yl]-2-oxo-ethyl]-phenyl]-acetyl]-4,4-difluoropyrrolidine-2-carboxylic acid

HRID 1636164Notes

Reaction equation

HRID 1636164 reaction equation
C([O:8][C:9]([C@H:11]1[CH2:15][C:14]([F:17])([F:16])[CH2:13][N:12]1[C:18](=[O:46])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([N:29]2[CH2:33][C:32]([F:35])([F:34])[CH2:31][C@@H:30]2[C:36]([O:38]CC2C=CC=CC=2)=[O:37])=[O:28])=[CH:22][CH:21]=1)=[O:10])C1C=CC=CC=1>C(O)C.[Pd]>[C:9]([C@H:11]1[CH2:15][C:14]([F:16])([F:17])[CH2:13][N:12]1[C:18](=[O:46])[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][C:27]([N:29]2[CH2:33][C:32]([F:35])([F:34])[CH2:31][C@@H:30]2[C:36]([OH:38])=[O:37])=[O:28])=[CH:24][CH:25]=1)([OH:10])=[O:8]

Participants

4

Reactant 1

HCID 53991841HCID 53991841, compound

Product 1

HCID 54227571(R)-1-[[4-[2-[(R)-2-carboxy-4,4-difluoropyrrolidin-1-yl]-2-oxo-ethyl]-phenyl]-acetyl]-4,4-difluoropyrrolidine-2-carboxylic acidYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.64 g (0.001 mol) (R)-1-[[4-[2-[(R)-2-Benzyloxycarbonyl-4,4-difluoropyrrolidin-yl]-2-oxo-ethyl]-phenyl]-acetyl]-4,4-difluoropyrrolidine-2-carboxlic acid benzyl ester in 20 ml ethanol were hydrogenated at room temperature and atmospheric pressure in the presence of 0.13 g 5% palladium/carbon. After completion of the reaction the catalyst was filtered off, the solvent was distilled off, and the residue was dissolved in dichloromethane. Evaporation gave 0.28 g (61%) (R)-1-[[4-[2-[(R)-2-carboxy-4,4-difluoropyrrolidin-1-yl]-2-oxo-ethyl]-phenyl]-acetyl]-4,4-difluoropyrrolidine-2-carboxylic acid as a light yellow foam. ISP-MS: 478 (MNH4)+; [α]D=+50.3° (c=0.33% in dimethylsulfoxide).

Workup

  1. customwere hydrogenated at room temperature
  2. customAfter completion of the reaction the catalyst
  3. filtrationwas filtered off
  4. distillationthe solvent was distilled off
  5. dissolutionthe residue was dissolved in dichloromethane
  6. customEvaporation

Sources & evidence

ORD record
ord-0717760def544b13bc99b39af78697c2
Source dataset
uspto-grants-2003_01
Patent number
US06512001B1

Reaction notes

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