Sodium Hydroxide → HCID 67352569、化合物

HRID 446835ノート

反応式

HRID 446835 の反応式
[CH2:1]([N:8]1[CH2:32][C@:31]2([C:33](=[O:36])CO)[C@@H:10]([CH2:11][C@H:12]3[C@H:25]4[C@@:16]([F:29])([C@:17]5([CH3:28])[C:22]([C@@H:23]([F:26])[CH2:24]4)=[CH:21][C:20](=[O:27])[CH:19]=[CH:18]5)[C@@H:15]([OH:30])[CH2:14][C@@:13]32[CH3:37])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:38].[Na+]>C1COCC1.O>[CH2:1]([N:8]1[CH2:32][C@:31]2([C:33]([OH:36])=[O:38])[C@@H:10]([CH2:11][C@H:12]3[CH:25]4[C@@:16]([F:29])([C@:17]5([CH3:28])[C:22]([C@@H:23]([F:26])[CH2:24]4)=[CH:21][C:20](=[O:27])[CH:19]=[CH:18]5)[C@@H:15]([OH:30])[CH2:14][C@@:13]32[CH3:37])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 53328064HCID 53328064、化合物

生成物 1

HCID 67352569HCID 67352569、化合物収率 33.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of compound 8 (460 mg, 0.899 mmol) and NaOH 6N (1350 μl, 11.10 mmol) in THF (20 ml) and water (10 ml) is stirred at RT for 3 days. Water is added and the organic solvent is evaporated. The basic aqueous solution (pH 12) is washed with AcOEt. The aqueous phase is then treated with HCl 6N until pH 6 when a solid precipitated. The solid is recovered by filtration and the aqueous phase is extracted with AcOEt, washed with brine, dried over Na2SO4 and then evaporated. The two fractions of obtained solid are combined and triturated with AcOEt (containing 2% MeOH) to give the title compound (150 mg, 0.301 mmol, 33.5% yield).

後処理

  1. customthe organic solvent is evaporated
  2. washThe basic aqueous solution (pH 12) is washed with AcOEt
  3. additionThe aqueous phase is then treated with HCl 6N until pH 6 when a solid
  4. customprecipitated
  5. filtrationThe solid is recovered by filtration
  6. extractionthe aqueous phase is extracted with AcOEt
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. customevaporated
  10. customtriturated with AcOEt (containing 2% MeOH)

出典と根拠

ORDレコード
ord-8715e6cc525648828537aa04808b1f6f
出典データセット
uspto-grants-2013_07
特許番号
US08481517B2

反応ノート

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