Water → 4-Carboxy-2-phenylbenzoyl methionine methyl ester

HRID 325231Notes

Reaction equation

HRID 325231 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C@H:4]([CH2:21][CH2:22][S:23][CH3:24])[NH:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][C:8]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CCN(CC[O:33][C:34]1C=CC(CC2C=CC=CC=2)=CC=1)CC.Cl.[C]=[O:49].O>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3](=[O:25])[C@H:4]([CH2:21][CH2:22][S:23][CH3:24])[NH:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][C:10]([C:34]([OH:33])=[O:49])=[CH:9][C:8]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 175534Tesmilifene HydrochlorideHCID 20622824(2-Phenyl4bromobenzoyl)-methionine methyl esterHCID 178418416HCID 178418416, compound

Product 1

HCID 206228254-Carboxy-2-phenylbenzoyl methionine methyl ester

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-bromo-2-phenylbenzoyl methionine methyl ester (1.0 equivalent), Pd(OAc)2 (0.05 equivalent) and DPPE (1.0 equivalent) is heated in DMF to 65° C. under 4 atm. of carbon monoxide until TLC analysis indicates that the reaction is complete. The reaction mixture is poured into water and extracted with ethyl acetate which is dried and evaporated. The product is purified by chromatography on silica gel.

Workup

  1. extractionextracted with ethyl acetate which
  2. customis dried
  3. customevaporated
  4. customThe product is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-cabf79b07c9c4cf2bbe4f00bfddb0db3
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Reaction notes

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