Potassium Carbonate → (S)-2-(Biphenyl-3-ylamino)-3-(3,4,5-trimethoxy-phenyl)-propionic acid

HRID 1920622Notes

Reaction equation

HRID 1920622 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:14][C@@H:15]([CH2:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=1)[C:16]([OH:18])=[O:17].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[Cu]I>[C:4]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=[C:2]([NH:14][C@@H:15]([CH2:19][C:20]2[CH:21]=[C:22]([O:30][CH3:31])[C:23]([O:28][CH3:29])=[C:24]([O:26][CH3:27])[CH:25]=2)[C:16]([OH:18])=[O:17])[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 164493-BromobiphenylHCID 21107851(2S)-2-Amino-3-(3,4,5-trimethoxyphenyl)propanoic acid

Product 1

HCID 11384247(S)-2-(Biphenyl-3-ylamino)-3-(3,4,5-trimethoxy-phenyl)-propionic acid

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

The title compound is prepared by heating a suspension of 3-bromo-biphenyl (1.47 mL, 8.54 mMol, Aldrich 25,538-6), (S)-2-amino-3-(3,4,5-trimethoxy-phenyl)-propionic acid (3,4,5-OCH3-phe-OH) (3.27 g, 12.81 mMol), K2CO3 (1.18 g, 8.54 mMol) and CuI (163 mg, 0.854 mMol) in DMF abs. (10.6 mL) for 24 h at 90° C., under an argon atmosphere. The resulting mixture is allowed to cool to rt, then concentrated in vacuo and purified by MPLC (CH3CN/H2O/TFA) to afford the title compound.

Workup

  1. customThe title compound is prepared
  2. temperatureby heating
  3. concentrationconcentrated in vacuo
  4. custompurified by MPLC (CH3CN/H2O/TFA)

Sources & evidence

ORD record
ord-fec4d4413bf147608e9023423ae00679
Source dataset
uspto-grants-2012_05
Patent number
US08173128B2

Reaction notes

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