HCID 54320997, compound → HCID 54406401, compound

HRID 1385716Notes

Reaction equation

HRID 1385716 reaction equation
C([O:8][C:9]([C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:44])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH2:26][C:27]([N:29]1[CH2:33][CH2:32][CH2:31][C@@H:30]1[C:34]([O:36]CC1C=CC=CC=1)=[O:35])=[O:28])=[O:10])C1C=CC=CC=1>C(O)C.[Pd]>[C:34]([C@H:30]1[CH2:31][CH2:32][CH2:33][N:29]1[C:27](=[O:28])[CH2:26][O:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[O:18][CH2:17][C:16]([N:12]1[CH2:13][CH2:14][CH2:15][C@@H:11]1[C:9]([OH:10])=[O:8])=[O:44])([OH:36])=[O:35]

Participants

4

Reactant 1

HCID 54320997HCID 54320997, compound

Product 1

HCID 54406401HCID 54406401, compoundYield 125.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

230 mg (0.38 mmol) (R)-1-[[2-[2-[(R)-2-benzyloxycarbonyl-pyrrolidin-1-yl]-2-oxo-ethoxy]-phenoxy]acetyl]pyrrolidine-2-carboxylic acid benzyl ester in 100 ml ethanol were hydrogenated in the presence of 30 mg 5% Pd on carbon. Filtration and evaporation of the solvent yielded 0.2 g (R)-1-[[2-[2-[(R)-2-carboxy-pyrrolidin-1-yl]-2-oxo-ethoxy]-phenoxy]acetyl]-pyrrolidine-2-carboxylic acid as colorless glass (that still contained small amounts of ethanol)

Workup

  1. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-3126639b2bf14e24ace78e0dfa53e4a8
Source dataset
uspto-grants-2001_07
Patent number
US06262089B1

Reaction notes

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