Methanol → HCID 21463545, compound

HRID 1940626Notes

Reaction equation

HRID 1940626 reaction equation
CO.C([O:5][C:6](=[O:24])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[S:13][C:14]2[C:20]([F:21])=[CH:19][C:18]([F:22])=[C:17]([F:23])[C:15]=2[N:16]=1)C.[OH-].[Na+]>O>[F:23][C:17]1[C:15]2[N:16]=[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([OH:24])=[O:5])[S:13][C:14]=2[C:20]([F:21])=[CH:19][C:18]=1[F:22]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 54536413HCID 54536413, compound

Product 1

HCID 21463545HCID 21463545, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To methanol (3 ml) was added 6-(4,5,7-trifluorobenzothiazol-2-yl)hexanoic acid ethyl ester (390 mg, 1.18 mmol) and aqueous 2N sodium hydroxide (0.7 ml, 1.4 mmol) and the mixture was stirred at room temperature for 1 hour. The resultant reaction mixture was diluted with water and washed with ether. The aqueous phase was acidified with 7% hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water, dried and then evaporated to yield a residue, which was crystallized from hexane-isopropyl ether to give 6-(4,5,7-trifluorobenzothiazol-2-yl)hexanoic acid (170 mg, 48%) as a colorless powder.

Workup

  1. customThe resultant reaction mixture
  2. washwashed with ether
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated
  7. customto yield a residue, which
  8. customwas crystallized from hexane-isopropyl ether

Sources & evidence

ORD record
ord-19a3bfc363f54a318169c60c2f1aa384
Source dataset
uspto-grants-1997_12
Patent number
US05700819

Reaction notes

Loading…