Hydrochloric Acid → HCID 24811558, compound

HRID 1945409Notes

Reaction equation

HRID 1945409 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11](=[O:25])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)[CH:5]=1.Cl>C1COCC1.O>[C:16]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:17]=[CH:18][C:13]([CH2:12][C:11]([NH:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:26])=[O:2])=[O:25])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 24811002HCID 24811002, compound

Product 1

HCID 24811558HCID 24811558, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

3-(2-biphenyl-4-yl-acetylamino)-benzoic acid methyl ester (133.6 mg, 0.39 mmol) in THF/H2O (1:1, 4 mL) was treated with LiOHH2O (32.7 mg, 0.78 mmol) at room temperature. The reaction mixture was then acidified with 10% HCl to PH 2. Resulting mixture was collected by filtration, and recrystallized with mixture of CH2Cl2 and MeOH to give 3-(2-biphenyl-4-yl-acetylamino)-benzoic acid as a white solid (74.4 mg, 58.1% yield).

Workup

  1. customResulting mixture
  2. filtrationwas collected by filtration
  3. customrecrystallized with mixture of CH2Cl2 and MeOH

Sources & evidence

ORD record
ord-a7a8601df3fa4536956ac68ab57d0253
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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