HCID 53940274, compound → HCID 54241570, compound

HRID 1385791Notes

Reaction equation

HRID 1385791 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-c8a0962f441e4813ade507fba10d2a6c
Source dataset
uspto-grants-2001_07
Patent number
US06262089B1

Reaction notes

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