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

HRID 383102Notes

Reaction equation

HRID 383102 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-089535082d7644e9af225ebee1e117c6
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

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