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

HRID 1160457노트

반응식

HRID 1160457 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-06a99a1256b843afab034fe3dbb44e1b
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816387B2

반응 노트

불러오는 중…