Water → HCID 57736447, compound

HRID 1641747Notes

Reaction equation

HRID 1641747 reaction equation
COC1C=CC(C[O:8][CH2:9][C:10]([O:12][CH2:13][NH:14][C:15]([C:17]2[CH:22]=[C:21]([CH3:23])[C:20]([CH:24]([C:35]3[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=3[F:42])[S:25]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)(=[O:27])=[O:26])=[CH:19][N:18]=2)=[O:16])=[O:11])=CC=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.O>ClCCl.O>[OH:8][CH2:9][C:10]([O:12][CH2:13][NH:14][C:15]([C:17]1[CH:22]=[C:21]([CH3:23])[C:20]([CH:24]([C:35]2[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=2[F:42])[S:25]([C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)(=[O:26])=[O:27])=[CH:19][N:18]=1)=[O:16])=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 57736496HCID 57736496, compound

Product 1

HCID 57736447HCID 57736447, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Procedure

To a mixed solution of [[[5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridin-2-yl]carbonyl]amino]methyl (4-methoxybenzyloxy)acetate (150 mg, 0.24 mmol) in dichloromethane-water (1:1, 10 ml), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (65 mg, 0.29 mmol) was added, and the mixture was stirred overnight at room temperature. Water was added to the reaction solution, and the mixture was extracted with dichloromethane. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, subsequently the solvent was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography. The fraction obtained from an elution with dichloromethane:methanol=50:3 was concentrated under reduced pressure, washed with diethyl ether, and collected by filtration, to obtain the title compound (26 mg, 0.05 mmol, 21%) as a white solid.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationsubsequently the solvent was concentrated under reduced pressure
  5. customThe fraction obtained from an elution with dichloromethane
  6. concentrationmethanol=50:3 was concentrated under reduced pressure
  7. washwashed with diethyl ether
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-d7d2f1c536134b29979ec15ce5ddab2a
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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