Sodium Carbonate → 5-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyrazine-2-carboxylic acid

HRID 1435829노트

반응식

HRID 1435829 반응식
C[O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([O:11][CH2:12][C:13]2[C:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:15][O:16][C:17]=2[CH3:18])=[CH:7][N:6]=1)=[O:4].[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:18][C:17]1[O:16][N:15]=[C:14]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]=1[CH2:12][O:11][C:8]1[N:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 14798Sodium Hydroxide2회HCID 426360595-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyrazine-2-carboxylic acid methyl ester

생성물 1

HCID 684440545-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyrazine-2-carboxylic acid수율 86%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
60 °C

실험 절차

To a solution of 5-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyrazine-2-carboxylic acid methyl ester (1.00 g, 3.07 mmol) (1.0 g, 1.69 mmol) in ethanol (10 mL) was added aqueous sodium hydroxide (1 N, 6.2 mL). After heating at 60° C. for 30 min it was cooled to ambient temperature and aqueous sodium carbonate (2 M, 50 mL) added. Addition of aqueous sodium hydroxide (1 M, 50 mL) was followed by extraction with tert-butylmethylether. The aqueous phase was acidified with aqueous hydrogen chloride (25%) to pH=2 and extracted with tert-butylmethylether and ethyl acetate. The combined organic layers were dried over sodium sulfate and concentration afforded the title compound (450 mg, 86%) as a white foam. MS: m/e=310.5 [M−H]−.

후처리

  1. temperaturewas cooled to ambient temperature
  2. extractionwas followed by extraction with tert-butylmethylether
  3. extractionextracted with tert-butylmethylether and ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate and concentration

출처 및 근거

ORD 기록
ord-c96772afa5724dd7b1aa3604164d039e
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618973B2

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