Methanol → (R)-4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanoic acid

HRID 1476262Notes

Reaction equation

HRID 1476262 reaction equation
[C:1]1([S:7][CH2:8][C@H:9]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([S:22](=[O:25])(=[O:24])[NH2:23])=[CH:18][C:17]=2[S:26]([C:29]([F:32])([F:31])[F:30])(=[O:28])=[O:27])[CH2:10][C:11]([O:13]C)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1COCC1.CO.[Li+].[OH-]>O>[C:1]1([S:7][CH2:8][C@H:9]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([S:22](=[O:24])(=[O:25])[NH2:23])=[CH:18][C:17]=2[S:26]([C:29]([F:30])([F:31])[F:32])(=[O:28])=[O:27])[CH2:10][C:11]([OH:13])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 66723774(R)-methyl 4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanoate2×

Product 1

HCID 66723519(R)-4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanoic acidYield 93.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 ml flask was charged with (R)-methyl 4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanoate (INTERMEDIATE 7, 7.5 g, 14.63 mmol) and THF (117 ml), MeOH (39 ml) and water (39 ml) were added sequentially. LiOH (1.05 g, 43.9 mmol) was added to the solution and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure to remove the volatiles, and cooled to 0° C. An aqueous solution of HCl (1N) was added dropwise to the solution and the resulting mixture was filtered. The filter cake was dried under high vacuum at 60° C. to provide the title product (6.8 g, yield: 93%).

Workup

  1. additionwere added sequentially
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto remove the volatiles
  4. temperaturecooled to 0° C
  5. additionAn aqueous solution of HCl (1N) was added dropwise to the solution
  6. filtrationthe resulting mixture was filtered
  7. customThe filter cake was dried under high vacuum at 60° C.

Sources & evidence

ORD record
ord-72c8529045f443a19b1769a0707359e9
Source dataset
uspto-grants-2015_04
Patent number
US09018381B2

Reaction notes

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