Hydrochloric Acid → HCID 59326575, compound

HRID 238631Notes

Reaction equation

HRID 238631 reaction equation
C[O:2][C:3](=[O:22])[CH2:4][C:5]1[CH:14]=[C:13]([S:15]C(=O)N(C)C)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:21])[CH:11]=2)[CH:6]=1.[OH-].[K+].Cl>CO.O>[F:21][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]=[C:5]([CH2:4][C:3]([OH:22])=[O:2])[CH:14]=[C:13]2[SH:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 59326500HCID 59326500, compound

Product 1

HCID 59326575HCID 59326575, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of (4-dimethylcarbamoylsulfanyl-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester (40 mg, 0.13 mmol) and potassium hydroxide (72 mg, 1.3 mmol) in methanol (10 mL) was heated at reflux for 3 hours. The resulting mixture was cooled to room temperature, diluted with water (10 mL), acidified with 2 N hydrochloric acid, and extracted with ethyl acetate (10 mL×2). The combined organic layers were washed with water and brine, then dried over sodium sulfate and concentrated in vacuo to afford crude (6-fluoro-4-mercapto-naphthalen-2-yl)-acetic acid (30 mg) as a yellow solid.

Workup

  1. temperatureat reflux for 3 hours
  2. extractionextracted with ethyl acetate (10 mL×2)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3de476ad37f44459b61ea85b4f6971d3
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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