Sodium Hydroxide → 1-(Benzyloxy carbonyl)pyrazolidine-3-carboxylic acid

HRID 1396842Notes

Reaction equation

HRID 1396842 reaction equation
[N:1]1([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:5][CH2:4][CH:3]([C:6]([O:8]C(C)(C)C)=[O:7])[NH:2]1.[OH-].[Na+]>Cl>[C:17]1([CH2:16][O:15][C:13]([N:1]2[CH2:5][CH2:4][CH:3]([C:6]([OH:8])=[O:7])[NH:2]2)=[O:14])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 133415401-Benzyl 3-tert-butyl 1,3-pyrazolidinedicarboxylate

Product 1

HCID 537448401-(Benzyloxy carbonyl)pyrazolidine-3-carboxylic acidYield 84%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of hydrogen chloride (10 L, 12.2% wt) charged into a 20-L, round-bottomed flask was added 3-(1,1-dimethylethyl) 1-(phenylmethyl) 1,3-pyrazolidinedicarboxylate (1000 g, 3.27 mol at room temperature. The mixture solution was heated at 35° C. for 4 h. The mixture solution was poured into 10 kg of ice and the pH was adjusted to 4 using aqueous NaOH (5M) solution. The product precipitated out and a filtration was performed to give the product (690 g, 1.32 mol, 84%) as a white solid.

Workup

  1. customThe product precipitated out
  2. filtrationa filtration

Sources & evidence

ORD record
ord-6914784edaf9401c8fcd9556afa4ee72
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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