HCID 53667158, compound → HCID 23557530, compound

HRID 1385792Notes

Reaction equation

HRID 1385792 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:48])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][CH2:28][C:29]([N:31]1[CH2:35][C:34]([F:37])([F:36])[CH2:33][C@@H:32]1[C:38]([O:40]CC1C=CC=CC=1)=[O:39])=[O:30])=[O:10])C1C=CC=CC=1>C(O)C.[Pd]>[C:9]([C@H:11]1[CH2:15][C:14]([F:17])([F:16])[CH2:13][N:12]1[C:18](=[O:48])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][CH2:28][C:29]([N:31]1[CH2:35][C:34]([F:37])([F:36])[CH2:33][C@@H:32]1[C:38]([OH:40])=[O:39])=[O:30])([OH:10])=[O:8]

Participants

4

Reactant 1

HCID 53667158HCID 53667158, compound

Product 1

HCID 23557530HCID 23557530, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.47 g (0.0007 mol) (R)-1-[[2-[2-[(R)-2-Benzyloxycarbonyl-4,4-difluoropyrrolidin-1-yl]-2-oxo-ethoxyl]-phenoxy]acetyl]-4,4-difluoropyrrolidine-2-carboxylic acid benzyl ester in 20 ml ethanol were hydrogenated at room temperature and atmospheric pressure in the presence of 0.09 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 0.32 g (94%) (R)-1-[[2-[2-[(R)-2-carboxy-4,4-difluoropyrrolidin-1-yl]-2-oxo-ethoxyl]-phenoxy]acetyl]-4,4difluoropyrrolidine-2-carboxylic acid as a light yellow foam. ISP-MS: 493 (MH)+; [α]D=+46.8° (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-3380fd434c3d4384818d95d463104422
Source dataset
uspto-grants-2001_07
Patent number
US06262089B1

Reaction notes

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