Lithium hydroxide, monohydrate → 5-[(3-{[(1S)-1-(hydroxymethyl)propyl]oxy}-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenyl)oxy]pyrazine-2-carboxylic acid

HRID 1989968노트

반응식

HRID 1989968 반응식
O.[OH-].[Li+].[OH:4][CH2:5][C@@H:6]([O:9][C:10]1[CH:11]=[C:12]([O:25][C:26]2[N:27]=[CH:28][C:29]([C:32]([O:34]C)=[O:33])=[N:30][CH:31]=2)[CH:13]=[C:14]([C:16]([NH:18][C:19]2[CH:23]=[CH:22][N:21]([CH3:24])[N:20]=2)=[O:17])[CH:15]=1)[CH2:7][CH3:8]>O.C1COCC1>[OH:4][CH2:5][C@@H:6]([O:9][C:10]1[CH:11]=[C:12]([O:25][C:26]2[N:27]=[CH:28][C:29]([C:32]([OH:34])=[O:33])=[N:30][CH:31]=2)[CH:13]=[C:14]([C:16]([NH:18][C:19]2[CH:23]=[CH:22][N:21]([CH3:24])[N:20]=2)=[O:17])[CH:15]=1)[CH2:7][CH3:8]

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 59127088methyl 5-[(3-{[(1S)-1-(hydroxymethyl)propyl]oxy}-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenyl)oxy]pyrazine-2-carboxylate

생성물 1

HCID 536296535-[(3-{[(1S)-1-(hydroxymethyl)propyl]oxy}-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenyl)oxy]pyrazine-2-carboxylic acid수율 46.8%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Lithium hydroxide monohydrate (6 mg, 0.14 mmol) in water (1 mL) was added to a solution of methyl 5-[(3-{[(1S)-1-(hydroxymethyl)propyl]oxy}-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenyl)oxy]pyrazine-2-carboxylate (25 mg, 0.06 mmol) in THF (1 mL). The mixture was allowed to stir at RT for 16 hours. The THF was removed in vacuo and the resulting solution was partitioned between water (10 mL) and ethyl acetate (25 mL), the ethyl acetate layer was washed with brine (10 mL) and dried (MgSO4). The aqueous layer was then adjusted to pH 7 by addition of 1M hydrochloric acid and extracted with ethyl acetate (25 mL). The ethyl acetate layer was washed with brine (10 mL) and dried (MgSO4). The ethyl acetate extracts were combined and evaporated to give the required product (12 mg). m/z 428.44 (M+H)+

후처리

  1. customThe THF was removed in vacuo
  2. customthe resulting solution was partitioned between water (10 mL) and ethyl acetate (25 mL)
  3. washthe ethyl acetate layer was washed with brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. additionThe aqueous layer was then adjusted to pH 7 by addition of 1M hydrochloric acid
  6. extractionextracted with ethyl acetate (25 mL)
  7. washThe ethyl acetate layer was washed with brine (10 mL)
  8. dry with materialdried (MgSO4)
  9. customevaporated

출처 및 근거

ORD 기록
ord-0ee0069594354c23a522ca8c13f1e71a
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07642263B2

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