Sodium Hydroxide → (3-(tert-butoxycarbonyl)-2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)acetic acid

HRID 1071046ノート

反応式

HRID 1071046 の反応式
C([O:3][C:4](=[O:27])[CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19][C:7]1=2)C.[OH-].[Na+]>CO>[C:23]([O:22][C:20]([N:17]1[CH2:16][CH2:15][C:8]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[N:6]([CH2:5][C:4]([OH:27])=[O:3])[C:7]=2[CH2:19][CH2:18]1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 22396754tert-butyl 6-(2-ethoxy-2-oxoethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

生成物 1

HCID 22396950(3-(tert-butoxycarbonyl)-2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)acetic acid収率 100.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

tert-Butyl 6-(2-ethoxy-2-oxoethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.606 g, 1.63 mmol) is dissolved in MeOH (20 mL) and 1N NaOH (2.44 mL, 2.44 mmol, 1.5 equiv.) is added. The resulting solution is stirred at rt for 3 h. The reaction mixture is concentrated and the residue is partitioned between EtOAc (50 mL) and 10% aqueous citric acid (30 mL). The layers are separated and the aqueous layer is extracted with EtOAc (25 mL). The combined organic layers are washed with water (2×15 mL) and brine (15 mL), dried over MgSO4, filtered and concentrated. Crude (3-(tert-butoxycarbonyl)-2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)acetic acid (0.566 g) is obtained in quantitative yield. 1H NMR (300 MHz, CDCl3) δ 1.49, 2.92-2.96, 3.00-3.04, 3.67-3.79, 4.83, 7.14, 7.19-7.20, 7.49; MS (ESI−) for C19H24N2O4 m/z 343.1 (M−H)31 .

後処理

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue is partitioned between EtOAc (50 mL) and 10% aqueous citric acid (30 mL)
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (25 mL)
  5. washThe combined organic layers are washed with water (2×15 mL) and brine (15 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-050bf94958b7431f8a01434caea4671c
出典データセット
uspto-grants-2005_06
特許番号
US06903090B2

反応ノート

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