Hydrochloric Acid → HCID 23132801, compound

HRID 2075479Notes

Reaction equation

HRID 2075479 reaction equation
C[O:2][C:3](=[O:33])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[C:18]([Br: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].Cl>C1COCC1.[OH-].[Na+].CO>[Br: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

6

Reactant 2

HCID 313Hydrochloric AcidHCID 66701018HCID 66701018, compound

Product 1

HCID 23132801HCID 23132801, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

96 mg 2-{[4-bromo-1-(4-trifluoromethyl-benzyloxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester in 0.5 ml THF, 0.56 ml of 2 M sodium hydroxide and 1.4 ml methanol were reacted in a microwave at 120° C. for 6 min. The reaction was then acidified with 2 M hydrochloric acid and extracted with ethyl acetate twice. The combined organic layers were dried over magnesium sulphate, and concentrated. After purification of the residue by RP-HPLC 11 mg of 2-{[4-Bromo-1-(4-trifluoromethyl-benzyloxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid were obtained.

Workup

  1. extractionextracted with ethyl acetate twice
  2. dry with materialThe combined organic layers were dried over magnesium sulphate
  3. concentrationconcentrated
  4. customAfter purification of the residue by RP-HPLC 11 mg of 2-{[4-Bromo-1-(4-trifluoromethyl-benzyloxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid
  5. customwere obtained

Sources & evidence

ORD record
ord-acd23c74872440eebdf2317b803f66f6
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

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