Methanol → HCID 22054074, compound

HRID 1830129Notes

Reaction equation

HRID 1830129 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:19])[CH2:13][C:14](=[CH2:18])[C:15]([OH:17])=[O:16])=[CH:8][CH:7]=1)(=[O:4])=[O:3].[CH2:20](S)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CO.O[O:31][S:32]([O-:34])=O.[K+]>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([C:12](=[O:19])[CH2:13][CH:14]([CH2:18][S:32]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:34])=[O:31])[C:15]([OH:17])=[O:16])=[CH:10][CH:11]=1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 887MethanolHCID 7509Benzyl mercaptanHCID 22053958HCID 22053958, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22054074HCID 22054074, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

4-(4-Methylsulfonylamino-phenyl)-2-methylene-4-oxo-butyric acid (800 mg, 2.83 mmol) was dissolved in DMF (5 mL). Benzyl mercaptan (0.5 mL, 4.25 mmol) and DMAP (200 mg, 1.6 mmol) were added. The mixture was stirred at ambient temperature for 16 hours. Methanol (200 mL) was added and, under vigorous stirring, a saturated aqueous solution of Oxone® (15 g, 24.4 mmol) was added in one portion. Stirring was continued for 2 hours. Methanol was removed under vacuum and the aqueous residue was diluted with 100 mL water. The crystallized product, 4-(4-Methylsulfonylamino-phenyl)-4-oxo-2-benzylsulfonylmethyl-butyric acid (380 mg), was filtered, washed with water, and dried under vacuum.

Workup

  1. stirringStirring
  2. waitwas continued for 2 hours
  3. customMethanol was removed under vacuum
  4. additionthe aqueous residue was diluted with 100 mL water
  5. filtrationThe crystallized product, 4-(4-Methylsulfonylamino-phenyl)-4-oxo-2-benzylsulfonylmethyl-butyric acid (380 mg), was filtered
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-f17cd9bccd884373aff76b8895986225
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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