Methanol → Methyl 3-(hydroxymethyl)-5-[methyl(methylsulfonyl)amino]benzoate

HRID 1160457Notes

Reaction equation

HRID 1160457 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([N:14]([CH3:19])[S:15]([CH3:18])(=[O:17])=[O:16])[CH:13]=1)[C:8](O)=[O:9])=[O:4].O1CCCC1.O1CCCC1.CO>O1CCCC1>[OH:9][CH2:8][C:7]1[CH:6]=[C:5]([CH:13]=[C:12]([N:14]([CH3:19])[S:15]([CH3:18])(=[O:17])=[O:16])[CH:11]=1)[C:3]([O:2][CH3:1])=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 111503713-(Methoxycarbonyl)-5-(N-methylmethylsulfonamido)benzoic acidHCID 22180045THF tetrahydrofurane

Product 1

HCID 57815142Methyl 3-(hydroxymethyl)-5-[methyl(methylsulfonyl)amino]benzoateYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(methoxycarbonyl)-5-[methyl(methylsulfonyl)amino]benzoic acid obtained in Reference Example 62.07 g (7.2 mmol) in tetrahydrofuran (10 mL) was added 1.0 M BH3.tetrahydrofuran/tetrahydrofuran solution 9 mL dropwise under ice-cooling and the mixture was stirred at room temperature for 16 hours. To the reaction solution was added methanol (3 mL) under ice-cooling, and the solvent was evaporated. To the residue was added water and the mixture was extracted with ethyl acetate. After drying of the mixture on magnesium sulfate, the solvent was evaporated and the resulting solid was recrystallized from chloroform/hexane to give 1.64 g (6.0 mmol) of the title compound (yield: 83%).

Workup

  1. additionwas added 1.0 M BH3
  2. temperaturecooling
  3. customthe solvent was evaporated
  4. additionTo the residue was added water
  5. extractionthe mixture was extracted with ethyl acetate
  6. customAfter drying of the mixture on magnesium sulfate
  7. customthe solvent was evaporated
  8. customthe resulting solid was recrystallized from chloroform/hexane

Sources & evidence

ORD record
ord-06a99a1256b843afab034fe3dbb44e1b
Source dataset
uspto-grants-2010_10
Patent number
US07816387B2

Reaction notes

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