Methanol → 5-(4,5,7-Trifluorobenzothiazol-2-ylthio)pentanoic acid

HRID 1940629Notes

Reaction equation

HRID 1940629 reaction equation
O1CCOCC1.CO.C([O:11][C:12](=[O:30])[CH2:13][CH2:14][CH2:15][CH2:16][S:17][C:18]1[S:19][C:20]2[C:26]([F:27])=[CH:25][C:24]([F:28])=[C:23]([F:29])[C:21]=2[N:22]=1)C.[OH-].[Na+]>O>[F:29][C:23]1[C:21]2[N:22]=[C:18]([S:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]([OH:30])=[O:11])[S:19][C:20]=2[C:26]([F:27])=[CH:25][C:24]=1[F:28]

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 538517315-(4,5,7-Trifluorobenzothiazol-2-ylthio)pentanoic acid ethyl ester

Product 1

HCID 214635625-(4,5,7-Trifluorobenzothiazol-2-ylthio)pentanoic acidYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of dioxane (5 ml), methanol (2.5 ml) and water (2.5 ml) was added 5-(4,5,7-trifluorobenzothiazol-2-ylthio)pentanoic acid ethyl ester (590 mg, 2 mmol) and sodium hydroxide (100 mg, 2.5 mmol) and the resultant mixture was stirred for 15 hours at room temperature. The reaction mixture was diluted with water and washed with ether. The aqueous phase was then acidified with 7% hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with an aqueous saturated saline solution, dried and then evaporated. The resulting oily residue was purified on a silica gel column and crystallized from hexane-isopropyl ether to give 5-(4,5,7-trifluorobenzothiazol-2-ylthio)pentanoic acid (170 mg, 31%) as a colorless powder.

Workup

  1. washwashed with ether
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with an aqueous saturated saline solution
  4. customdried
  5. customevaporated
  6. customThe resulting oily residue was purified on a silica gel column
  7. customcrystallized from hexane-isopropyl ether

Sources & evidence

ORD record
ord-5999f821c0df46ca81ebb8073398dfee
Source dataset
uspto-grants-1997_12
Patent number
US05700819

Reaction notes

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