Citric Acid → HCID 18476063, compound

HRID 2187624Notes

Reaction equation

HRID 2187624 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:27][CH2:28][CH2:29][N:30]2[CH:34]=[CH:33][N:32]=[CH:31]2)[C:9]2[CH:10]=[CH:11][C:12]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[C:13]([CH:18]=2)[C:14]([O:16]C)=[O:15])=[CH:4][CH:3]=1.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:27][CH2:28][CH2:29][N:30]2[CH:34]=[CH:33][N:32]=[CH:31]2)[C:9]2[CH:10]=[CH:11][C:12]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[C:13]([CH:18]=2)[C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 962WaterHCID 18476009HCID 18476009, compound

Product 1

HCID 18476063HCID 18476063, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 5-[1-(4-fluorophenyl)-2-(imidazol-1-yl)ethylaminomethyl]-2-(4-fluorobenzyl)benzoate (1.5 g) sodium hydroxide (0.65 g), water (10 ml) and methanol (50 ml) was stirred under an inert atmosphere at ambient temperature for 2 hours. It was then acidified to pH 4-5 with 1M citric acid and evaporated to dryness. The residue was partitioned between ethyl acetate and water, the organic layer separated, treated with saturated brine, dried and evaporated to dryness to give 5-[1-(4-fluorophenyl)-2-(imidazol-1-yl)ethylaminomethyl]-2-(4-fluorobenzyl)benzoic acid as a white foam (1.0 g).

Workup

  1. customevaporated to dryness
  2. customThe residue was partitioned between ethyl acetate and water
  3. customthe organic layer separated
  4. additiontreated with saturated brine
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-360d65034dbd42be901fe0dc9754bc5f
Source dataset
uspto-grants-2002_06
Patent number
US06410539B1

Reaction notes

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