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 1969637노트

반응식

HRID 1969637 반응식
[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]

참가 물질

4

반응물 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

생성물 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)cyclopentanol수율 98.2%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-781dcf4db98f482c8355d9668d1dac0d
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426411B2

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