Methanol → 4-Morpholin-4-yl-4-oxo-2-(2-trifluoromethyl-benzylsulfonylmethyl)-butyric acid

HRID 1830126Notes

Reaction equation

HRID 1830126 reaction equation
[CH2:1]=[C:2]([CH2:6][C:7]([N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[O:8])[C:3]([OH:5])=[O:4].[F:15][C:16]([F:26])([F:25])[C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19]S.CO.O[O:30][S:31]([O-:33])=O.[K+]>CN(C=O)C.CN(C1C=CN=CC=1)C>[N:9]1([C:7](=[O:8])[CH2:6][CH:2]([CH2:1][S:31]([CH2:19][C:18]2[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=2[C:16]([F:15])([F:25])[F:26])(=[O:33])=[O:30])[C:3]([OH:5])=[O:4])[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1

Participants

7

Reactant 4

HCID 887MethanolHCID 27614232-(Trifluoromethyl)phenylmethanethiolHCID 220540222-Methylene4-morpholin-4-yl-4-oxo-butyric acidHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 220539894-Morpholin-4-yl-4-oxo-2-(2-trifluoromethyl-benzylsulfonylmethyl)-butyric acid

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-methylene-4-morpholin-4-yl-4-oxo-butyric acid (2 g, 10.03 mmol), in DMF (5 mL), 2-trifluoromethylbenzyl mercaptan (1.93 g, 10.03 mmol) and DMAP (122 mg, 1.0 mmol) was stirred at ambient temperature for 16 hours. Methanol (200 mL) and a saturated aqueous solution of Oxone® (20 g, 32.5 mmol) were added with continued stirring for 2 hours. Methanol was removed under vacuum and the aqueous residue was diluted with 200 mL of water. The crystallized product was filtered, washed with water, and dried under vacuum to yield 4-morpholin-4-yl-4-oxo-2-(2-trifluoromethyl-benzylsulfonylmethyl)-butyric acid (0.95 g) as a white solid.

Workup

  1. customMethanol was removed under vacuum
  2. additionthe aqueous residue was diluted with 200 mL of water
  3. filtrationThe crystallized product was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-d2b151c39d9a41da90bb419d88fb61a9
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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