Ammonium formate → (4-Amino-2-phenylbenzoyl)methionine 2-trimethylsilylethyl ester

HRID 2121223Notes

Reaction equation

HRID 2121223 reaction equation
[CH3:1][Si:2]([CH3:32])([CH3:31])[CH2:3][CH2:4][O:5][C:6](=[O:30])[C@H:7]([CH2:26][CH2:27][S:28][CH3:29])[NH:8][C:9](=[O:25])[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:11]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:32][Si:2]([CH3:1])([CH3:31])[CH2:3][CH2:4][O:5][C:6](=[O:30])[C@H:7]([CH2:26][CH2:27][S:28][CH3:29])[NH:8][C:9](=[O:25])[C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:11]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69844218(4-Nitro-2-phenylbenzoyl)methionine 2-trimethylsilylethyl ester

Product 1

HCID 67550574(4-Amino-2-phenylbenzoyl)methionine 2-trimethylsilylethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of the product of Example 283A (8.85 g, 25.8 mmol), ammonium formate (4.88 g, 77.4 mmol) and palladium (10%) on carbon (1 g) in methanol was refluxed for 5 hours. The mixture was then filtered through Celite and rinsed with ethyl acetate. The filtrate was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the title compound which was used without further purification.

Workup

  1. temperaturewas refluxed for 5 hours
  2. filtrationThe mixture was then filtered through Celite
  3. washrinsed with ethyl acetate
  4. additionThe filtrate was diluted with ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a5c1f65ed5144c3abc186affb8e82401
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

Loading…