HCID 68978349, compound → HCID 68861461, compound

HRID 1784232Notes

Reaction equation

HRID 1784232 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C@@H:4]([NH:20][C:21](=[O:30])[C:22]1[CH:27]=[C:26](Br)[CH:25]=[CH:24][C:23]=1[OH:29])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]CC2C=CC=CC=2)=[CH:8][CH:7]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:31])[C@@H:4]([NH:20][C:21](=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[OH:29])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([OH:12])=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 68978349HCID 68978349, compound

Product 1

HCID 68861461HCID 68861461, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-3-(4-benzyloxy-phenyl)-2-(5-bromo-2-hydroxy-benzoylamino)-propionic acid methyl ester (750 mg, 1.5 mmol) was dissolved in 30 mL of MeOH, 100 mg of 10% Pd/C added, and the mixture stirred for 2.5 h under 40 psi of H2. The mixture was filtered and solvent evaporated. The resulting residue was dissolved in DCM, washed with saturated NaHCO3, dried over sodium sulfate and evaporated to give (S)-2-(2-hydroxy-benzoylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester (409 mg).

Workup

  1. filtrationThe mixture was filtered
  2. customsolvent evaporated
  3. dissolutionThe resulting residue was dissolved in DCM
  4. washwashed with saturated NaHCO3
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-700ce5cf756c4b6ab432a032d6163755
Source dataset
uspto-grants-2009_03
Patent number
US07501538B2

Reaction notes

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