Benzyl chloroformate → Benzyl (S)-2-(6-hydroxy-1H-indazol-1-yl)-1-methylethylcarbamate

HRID 1453890

반응식

HRID 1453890 반응식
[NH2:1][C@@H:2]([CH3:14])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[CH:6]=[N:5]1.C(=O)(O)[O-].[Na+].Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>C1COCC1>[CH2:24]([O:23][C:21](=[O:22])[NH:1][C@@H:2]([CH3:14])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[CH:6]=[N:5]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

참가 물질

5

반응물 3

HCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate2회HCID 135453290AL-34662

생성물 1

HCID 135487328Benzyl (S)-2-(6-hydroxy-1H-indazol-1-yl)-1-methylethylcarbamate수율 78%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

1-((S)-2-Aminopropyl)-1H-indazol-6-ol [prepared in accordance with commonly owned WO 02/098862A1, the contents of which are by this reference incorporated herein] (2.00 g, 10.5 mmol) was suspended in THF (20 mL) and saturated aqueous sodium bicarbonate (10 mL) and benzyl chloroformate (1.50 mL, 15 mol) were added. The mixture was stirred at room temperature until the starting amine dissolved. Saturated aqueous sodium bicarbonate (150 mL) was added and the reaction mixture extracted with ethyl acetate (3×150 mL). The combined organic layers were dried (magnesium sulfate), filtered, and evaporated to give a tan foam (2.65 g, 78%) which was pure by LC/MS (+APCI) m/z 326 (M+H+).

후처리

  1. dissolutiondissolved
  2. extractionthe reaction mixture extracted with ethyl acetate (3×150 mL)
  3. dry with materialThe combined organic layers were dried (magnesium sulfate)
  4. filtrationfiltered
  5. customevaporated

출처 및 근거

ORD 기록
ord-700e0b1c960943d5a6582988383acb11
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476687B2

연결된 노트

불러오는 중…