HCID 53940274, compound → HCID 54241570, compound

HRID 1636162Notes

Reaction equation

HRID 1636162 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:42])[CH2:19][CH2:20][CH2:21][CH2:22][C:23]([N:25]1[CH2:29][C:28]([F:31])([F:30])[CH2:27][C@@H:26]1[C:32]([O:34]CC1C=CC=CC=1)=[O:33])=[O:24])=[O:10])C1C=CC=CC=1>C(O)C.[Pd]>[C:32]([C@H:26]1[CH2:27][C:28]([F:30])([F:31])[CH2:29][N:25]1[C:23](=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][C:18]([N:12]1[CH2:13][C:14]([F:16])([F:17])[CH2:15][C@@H:11]1[C:9]([OH:10])=[O:8])=[O:42])([OH:34])=[O:33]

Participants

4

Reactant 1

HCID 53940274HCID 53940274, compound

Product 1

HCID 54241570HCID 54241570, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.59 g (0.001 mol) (R)-1-[6-[(R)-2-Benzyloxycarbonyl-4,4-difluoro-pyrrolidin-1-yl]-6-oxo-hexanoyl]-4,4-difluoropyrrolidine-2-carboxylic acid benzyl ester in 20 ml ethanol were hydrogenated at room temperature and atmospheric pressure in the presence of 0.12 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 0.4 g (97%) (R)-1-[6-[(R)-2-carboxy-4,4-difluoro-pyrrolidin-1-yl]-6-oxo-hexanoyl]-4,4-difluoropyrrolidine-2-carboxylic acid as a white foam. ISP-MS: 413 (MH)+; [α]D=+54.2° (c=1% 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-2049b384de254853a9fdbd63303fedd8
Source dataset
uspto-grants-2003_01
Patent number
US06512001B1

Reaction notes

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