Sodium Hydroxide → 3-(Methoxycarbonyl)-5-(N-methylmethylsulfonamido)benzoic acid

HRID 2071119ノート

反応式

HRID 2071119 の反応式
[CH3:1][N:2]([C:7]1[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[CH:10]=[C:11]([CH:16]=1)[C:12]([O:14]C)=[O:13])[S:3]([CH3:6])(=[O:5])=[O:4].[OH-].[Na+]>C1COCC1.CO.O>[CH3:20][O:19][C:17]([C:9]1[CH:10]=[C:11]([CH:16]=[C:7]([N:2]([CH3:1])[S:3]([CH3:6])(=[O:5])=[O:4])[CH:8]=1)[C:12]([OH:14])=[O:13])=[O:18]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 11324067Dimethyl 5-(N-methylmethylsulfonamido)isophthalate

生成物 1

HCID 111503713-(Methoxycarbonyl)-5-(N-methylmethylsulfonamido)benzoic acid収率 75%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

Dimethyl 5-(N-methylmethylsulfonamido)isophthalate (0.842 g, 2.8 mmol) was dissolved in THF:MeOH (1:1) (8 mL) and H2O (3 mL). Solid NaOH (0.112 g, 2.8 mmol) was added and stirred at room temperature for 18 h. The reaction mixture was concentrated under reduced pressure. Saturated NaHCO3 (10 mL) was added to the reaction mixture and extracted with toluene (to remove <10% unreacted starting material). The aqueous solution was acidified with dilute HCl (10%), extracted with EtOAc, and dried over anhydrous Na2SO4. The solvent was evaporated and dried under reduced pressure to give 3-(methoxycarbonyl)-5-(N-methylmethylsulfonamido)benzoic acid as a white solid (75%, 0.598 g), which was used without further purification.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionSaturated NaHCO3 (10 mL) was added to the reaction mixture
  3. extractionextracted with toluene (to remove <10% unreacted starting material)
  4. extractionextracted with EtOAc
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was evaporated
  7. customdried under reduced pressure

出典と根拠

ORDレコード
ord-65840668ed584f76ab0e7955ecb0ed9f
出典データセット
uspto-grants-2012_10
特許番号
US08299267B2

反応ノート

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