Sodium Hydroxide → 4-[4-(2-Adamantylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoic acid

HRID 1799360노트

반응식

HRID 1799360 반응식
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([C:14]1[CH:15]=[N:16][N:17]([C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=3)[C:18]=1[S:19][CH2:20][CH2:21][CH3:22])=[O:13])[CH2:8]2.[OH-].[Na+]>CO>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([C:14]1[CH:15]=[N:16][N:17]([C:23]3[CH:32]=[CH:31][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=3)[C:18]=1[S:19][CH2:20][CH2:21][CH3:22])=[O:13])[CH2:8]2

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 53630271Methyl 4-[4-(2-adamantylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate2회

생성물 1

HCID 250055784-[4-(2-Adamantylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoic acid

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Methyl 4-[4-(2-adamantylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate (190 mg, 0.42 mmol) (Intermediate #2) was dissolved in methanol (10 mL) and treated at ambient temperature with 2M aqueous sodium hydroxide solution (1.05 mL, 2.1 mmol). The mixture was stirred at ambient temperature for 18 h. and then heated to 65° C. for a further 2 h. Methanol was removed by evaporation under reduced pressure and the clear solution diluted with water (25 ml). 2M HCl was added to pH4 and the mixture extracted with ethyl acetate (2×25 mL). The combined extracts were washed with water (2×10 mL) and brine (10 mL), dried (MgSO4) and evaporated to give the title compound as a white solid. (174 mg, 94%)

후처리

  1. temperatureheated to 65° C. for a further 2 h
  2. customMethanol was removed by evaporation under reduced pressure
  3. additionthe clear solution diluted with water (25 ml)
  4. addition2M HCl was added to pH4
  5. extractionthe mixture extracted with ethyl acetate (2×25 mL)
  6. washThe combined extracts were washed with water (2×10 mL) and brine (10 mL)
  7. dry with materialdried (MgSO4)
  8. customevaporated

출처 및 근거

ORD 기록
ord-1009b57a74254286ad033bcf1f6aeb83
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344016B2

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