Hydrochloric Acid → HCID 23132837, compound

HRID 2075494Notes

Reaction equation

HRID 2075494 reaction equation
C[O:2][C:3](=[O:33])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[C:18]([F:20])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1)=[O:9])([CH3:6])[CH3:5].C1COCC1.[OH-].[Na+].Cl>O.C(OCC)(=O)C.CO>[F:20][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:28]=2)=[C:10]([C:8]([NH:7][C:4]([CH3:6])([CH3:5])[C:3]([OH:33])=[O:2])=[O:9])[CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66701197HCID 66701197, compound

Product 1

HCID 23132837HCID 23132837, compoundYield 23.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 22728543Water ethylacetateSolvent

Procedure

To 0.198 g of 2-{[4-fluoro-1-(4-trifluoromethyl-benzyloxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester was added 15 ml of THF and 5 ml of methanol followed by 5 ml of 1M NaOH. The solution was stirred at ambient temperature for 12 h. The reaction mixture was poured into water/ethyl acetate, acidified to pH 1-2 with 1M HCl, extracted with ethyl acetate, washed with water, dried (sodium sulphate), filtered and concentrated to a colorless oil which crystallized on standing. The material was triturated with ether, filtered and dried at 50° C. for 1.5 h to provide 45 mg of 2-{[4-fluoro-1-(4-trifluoromethyl-benzyloxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried (sodium sulphate)
  4. filtrationfiltered
  5. concentrationconcentrated to a colorless oil which
  6. customcrystallized
  7. customThe material was triturated with ether
  8. filtrationfiltered
  9. customdried at 50° C. for 1.5 h

Sources & evidence

ORD record
ord-6cbf823f6b83479498c533035605ca0f
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

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