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 1989968ノート

反応式

HRID 1989968 の反応式
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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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)+

後処理

  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

出典と根拠

ORDレコード
ord-0ee0069594354c23a522ca8c13f1e71a
出典データセット
uspto-grants-2010_01
特許番号
US07642263B2

反応ノート

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