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

HRID 1453890

Reaction equation

HRID 1453890 reaction equation
[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

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate2×HCID 135453290AL-34662

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-700e0b1c960943d5a6582988383acb11
Source dataset
uspto-grants-2009_01
Patent number
US07476687B2

Linked notes

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