Hydrochloric Acid → HCID 68998448, compound

HRID 1987982Notes

Reaction equation

HRID 1987982 reaction equation
[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:14]([O:16]C)=[O:15])[CH:10]=[C:11]([F:13])[CH:12]=3)[N:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+].Cl>CO>[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:14]([OH:16])=[O:15])[CH:10]=[C:11]([F:13])[CH:12]=3)[N:8]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69002715HCID 69002715, compound

Product 1

HCID 68998448HCID 68998448, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the ester from Step E (115 mg, 0.49 mmol), 2 N NaOH (2.0 mL, 4.0 mmol), and methanol (5 mL) was stirred at room temperature under nitrogen for 2 h. The reaction mixture was acidified with 1 N HCl, extracted with methylene chloride, washed with brine, dried over sodium sulfate, filtered and concentrated to afford 2-cyclopropyl-6-fluorobenzoxazole-4-carboxylic acid (105 mg, 97%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 12.90 (br s, 1H), 7.91 (dd, J=8.1, 2.4 Hz, 1H), 7.58 (dd, J=10.2, 2.4 Hz, 1H), 2.39-2.29 (m, 1H), 1.25-1.14 (m, 4H); 19F NMR (282 MHz, CDCl3) δ −116.79; MS (ESI+) m/z 222 (M+H).

Workup

  1. extractionextracted with methylene chloride
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-db0d590e05c64a4dbacd50070a882594
Source dataset
uspto-grants-2009_06
Patent number
US07553846B2

Reaction notes

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