Sodium Hydroxide → [5-tert-Butyl-2-(3-hydroxy-propyl)-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloroethyl ester

HRID 75626Notes

Reaction equation

HRID 75626 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][CH2:9][OH:10])[N:5]=[C:4]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:3]=1.[OH-].[Na+].Cl[C:18]([O:20][CH2:21][C:22]([Cl:25])([Cl:24])[Cl:23])=[O:19]>CCOC(C)=O>[Cl:23][C:22]([Cl:25])([Cl:24])[CH2:21][O:20][C:18](=[O:19])[NH:1][C:2]1[N:6]([CH2:7][CH2:8][CH2:9][OH:10])[N:5]=[C:4]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 866867313-(5-Amino-3-tert-butyl-pyrazol-1-yl)-propan-1-ol

Product 1

HCID 86686732[5-tert-Butyl-2-(3-hydroxy-propyl)-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloroethyl esterYield 63.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of Intermediate 35a (0.94 g, 4.76 mmol) in EtOAc (15 mL) was treated with aqueous NaOH (1M, 8.58 mmol), followed by 2,2,2-trichloroethyl chloroformate (0.79 mL, 5.72 mmol) and stirred at RT for 1.5 h. The two layers were separated, and the organic layer was washed with water (2×10 mL), dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a white solid (1.12 g, 63%). LCMS (Method 3): Rt 3.72 min, m/z 372/374 [MH+].

Workup

  1. customThe two layers were separated
  2. washthe organic layer was washed with water (2×10 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a2a062868e7845818b227bd3b51cf4ca
Source dataset
uspto-grants-2014_09
Patent number
US08835431B2

Reaction notes

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