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

HRID 600474노트

반응식

HRID 600474 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-379c8cd21f2a4a0f8aa382f7f637b56a
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902201B2

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