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

HRID 1160457ノート

反応式

HRID 1160457 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-06a99a1256b843afab034fe3dbb44e1b
出典データセット
uspto-grants-2010_10
特許番号
US07816387B2

反応ノート

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