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

HRID 1061622Notes

Reaction equation

HRID 1061622 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-74fd3aa3131a4eb494ebb23f8d474526
Source dataset
uspto-grants-2005_11
Patent number
US06960593B2

Reaction notes

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