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

HRID 1815970

Reaction equation

HRID 1815970 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>[OH:13][C:10]1[CH:11]=[C:12]2[C:7]([CH:6]=[N:5][N:4]2[CH2:3][C@@H:2]([NH:1][C:21](=[O:22])[O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH3:14])=[CH:8][CH:9]=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 543%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1-((S)-2-aminopropyl)-1H-indazol-6-ol (2.00 g, 10.5 mmol) in THF (20 mL) was added saturated aqueous sodium bicarbonate (10 mL) and benzyl chloroformate (1.50 mL, 1.5 mmol). The mixture was stirred until all of the solid starting amine dissolved. After stirring at ambient temperature for 45 minutes saturated aqueous sodium bicarbonate (150 mL) was added and the mixture was extracted with ethyl acetate (3×150 mL). The combined extracts were dried (MgSO4) and evaporated to give a tan foam (2.65 g, 78%): LC/MS (+APCI) m/z 326 (M+H).

Workup

  1. dissolutiondissolved
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate (3×150 mL)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-a8a19e51dcec4122a09882618fe5603a
Source dataset
uspto-grants-2005_04
Patent number
US06881749B2

Linked notes

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