Sodium Hydroxide → 3-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanol

HRID 1969637ノート

反応式

HRID 1969637 の反応式
[OH-].[Na+].C([O:11][CH:12]1[CH2:16][CH:15]([C:17]2[N:21]3[C:22]4[CH:28]=[CH:27][N:26]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:23]=4[N:24]=[CH:25][C:20]3=[N:19][N:18]=2)[CH:14]([CH2:37][CH3:38])[CH2:13]1)(=O)C1C=CC=CC=1>CO>[CH2:37]([CH:14]1[CH:15]([C:17]2[N:21]3[C:22]4[CH:28]=[CH:27][N:26]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:34])([CH3:36])[CH3:35])[C:23]=4[N:24]=[CH:25][C:20]3=[N:19][N:18]=2)[CH2:16][CH:12]([OH:11])[CH2:13]1)[CH3:38]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 585578993-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl benzoate

生成物 1

HCID 585572033-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanol収率 98.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

To a solution of NaOH (0.088 g, 2.20 mmol) in MeOH (8 mL) was added a solution of 3-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl benzoate (0.158 g, 0.312 mmol, prepared using KK from Preparation #20.2) in MeOH (2 mL). The reaction mixture was stirred at ambient temperature for about 3 h. The solvent was removed under reduced pressure and DCM (150 mL) was added. The organic layer was washed with water (5 mL), saturated aqueous NaHCO3 (15 mL), brine (15 mL), and dried over anhydrous MgSO4, filtered, and concd under reduced pressure to give 3-ethyl-4-(6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanol (0.123 g, 98%) as clear oil: LC/MS (Table 1, Method b) Rt=2.34 min; MS m/z: 402 (M+H)+.

後処理

  1. customThe solvent was removed under reduced pressure and DCM (150 mL)
  2. additionwas added
  3. washThe organic layer was washed with water (5 mL), saturated aqueous NaHCO3 (15 mL), brine (15 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered

出典と根拠

ORDレコード
ord-781dcf4db98f482c8355d9668d1dac0d
出典データセット
uspto-grants-2013_04
特許番号
US08426411B2

反応ノート

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