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

HRID 2071119노트

반응식

HRID 2071119 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 21899815MeOH tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-65840668ed584f76ab0e7955ecb0ed9f
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299267B2

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