Acetic Acid → HCID 22860068, compound

HRID 1720511Notes

Reaction equation

HRID 1720511 reaction equation
C([O:8][C:9]1[CH:40]=[CH:39][C:12]([O:13][CH2:14][C:15]([C@@H:17]2[CH2:21][CH2:20][CH2:19][N:18]2[C:22](=[O:38])[C@@H:23]2[CH2:27][CH2:26][CH2:25][N:24]2[C:28](=[O:37])[CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:16])=[CH:11][CH:10]=1)C1C=CC=CC=1.O.C(O)(=O)C>CO.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][C:15]([C@@H:17]2[CH2:21][CH2:20][CH2:19][N:18]2[C:22](=[O:38])[C@@H:23]2[CH2:27][CH2:26][CH2:25][N:24]2[C:28](=[O:37])[CH2:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:16])=[CH:39][CH:40]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 67771615HCID 67771615, compound

Product 1

HCID 22860068HCID 22860068, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2S)-2-[4-(benzyloxy)phenoxyacetyl]-1-[N-(3-phenylpropionyl)-L-prolyl]pyrrolidine (1.44 g) in a mixture of methanol (50 ml), water (30 ml) and acetic acid (20 ml) was added Pd-Black (300 mg), and the mixutre was stirred at room temperature under hydrogen atmosphere for 4 hours. The reaction mixture was concentrated, and the concentrate was poured into saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluate: chloroform-methanol) to give 0.71 g of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe concentrate was poured into saturated aqueous solution of sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (eluate: chloroform-methanol)

Sources & evidence

ORD record
ord-ea93d412c6dd42448ccbbd2418dc8d24
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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