Sodium Hydroxide → N-[3-(4,5,7-trifluorobenzothiazol-2-yl)propionyl]-N-methylglycine

HRID 1940612Notes

Reaction equation

HRID 1940612 reaction equation
C([O:3][C:4](=[O:24])[CH2:5][N:6]([C:8](=[O:23])[CH2:9][CH2:10][C:11]1[S:12][C:13]2[C:19]([F:20])=[CH:18][C:17]([F:21])=[C:16]([F:22])[C:14]=2[N:15]=1)[CH3:7])C.[OH-].[Na+]>CO.O>[F:22][C:16]1[C:14]2[N:15]=[C:11]([CH2:10][CH2:9][C:8]([N:6]([CH3:7])[CH2:5][C:4]([OH:24])=[O:3])=[O:23])[S:12][C:13]=2[C:19]([F:20])=[CH:18][C:17]=1[F:21]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21463533N-[3-(4,5,7-trifluorobenzothiazol-2-yl)propionyl]-N-methylglycine ethyl ester

Product 1

HCID 21463526N-[3-(4,5,7-trifluorobenzothiazol-2-yl)propionyl]-N-methylglycineYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of N-[3-(4,5,7-trifluorobenzothiazol-2-yl)propionyl]-N-methylglycine ethyl ester (290 mg, 0.8 mmol) in methanol (2 ml) was added 2N sodium hydroxide (0.5 ml, 1 mmol) and the mixture was stirred for 30 min. at room temperature. The reaction mixture was diluted with water and then washed with ether. The aqueous layer was acidified with 7% hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, then dried and evaporated to yield a residue, which was recrystallized from ethanol-isopropyl ether to give N-[3-(4,5,7-trifluorobenzothiazol-2-yl)propionyl]-N-methylglycine (185 mg, 70%).

Workup

  1. washwashed with ether
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. customevaporated
  6. customto yield a residue, which
  7. customwas recrystallized from ethanol-isopropyl ether

Sources & evidence

ORD record
ord-7e6977eeb76b461c8369f188539c303c
Source dataset
uspto-grants-1997_12
Patent number
US05700819

Reaction notes

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