Acetic Acid → HCID 21311230, compound

HRID 1584084Notes

Reaction equation

HRID 1584084 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]([NH:5][C@@H:6]([CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH3:21])=[CH:15][CH:14]=1)=O)[C:7]([OH:9])=[O:8])=[O:4].C(O)(=O)C.[H][H]>C(OCC)(=O)C.[Pd]>[F:1][C:2]([F:22])([F:23])[C:3]([NH:5][C@@H:6]([CH2:10][CH2:11][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][CH3:21])=[CH:17][CH:18]=1)[C:7]([OH:9])=[O:8])=[O:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 21311229HCID 21311229, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21311230HCID 21311230, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-trifluoroacetyl-α-(S)-(2-(4-n-propylphenyl)-2-oxoethyl)glycine 6 (140 mg, 0.43 mmol) in ethyl acetate (10 mL) containing acetic acid (0.25 mL) and 10% palladium on carbon (10 mg) was stirred under one atmosphere of hydrogen gas. After two days, the catalyst was filtered off and fresh catalyst was added and the reaction stirred under hydrogen overnight. The mixture was filtered and the solvent evaporated in vacuo to yield the product 7 (127 mg, 93% yield).

Workup

  1. filtrationthe catalyst was filtered off
  2. additionfresh catalyst was added
  3. filtrationThe mixture was filtered
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-410530a249734a219a8860d779631c2f
Source dataset
uspto-grants-1999_08
Patent number
US05932551

Reaction notes

Loading…