Hydrochloric Acid → 4-(2,2-Dimethylpropionyloxy)pyrazolidine-1-carboxylic acid 1-benzyl ester

HRID 7656

Reaction equation

HRID 7656 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([O:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:10][N:9]1[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])=O)(C)(C)C.S(Cl)(Cl)=O.Cl>CO>[CH2:23]([O:22][C:20]([N:9]1[CH2:10][CH:11]([O:13][C:14](=[O:19])[C:15]([CH3:17])([CH3:16])[CH3:18])[CH2:12][NH:8]1)=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 207247514-(2,2-Dimethylpropionyloxy)pyrazolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

Product 1

HCID 207247484-(2,2-Dimethylpropionyloxy)pyrazolidine-1-carboxylic acid 1-benzyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

4-(2,2-Dimethylpropionyloxy)pyrazolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester, 29, (1.76 g, 4.33 mmol) is dissolved in methanol (40 mL) and the solution cooled to 0° C. Thionyl chloride (3.16 mL, 43.3 mmol) is added dropwise and the reaction allowed to warm to room temperature and continue stirring 12 hours. The reaction solution is concentrated in vacuo to give afford 1.45 g (98% yield) of the desired product as the HCl salt as an off-white solid.

Workup

  1. temperatureto warm to room temperature
  2. concentrationThe reaction solution is concentrated in vacuo
  3. customto give

Sources & evidence

ORD record
ord-95bc99090f3e498c8ea0e5f42c1b5fc5
Source dataset
uspto-grants-2006_08
Patent number
US07087615B2

Linked notes

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