Water → 1-[(2-Propen-1-yloxy)carbonyl]-3-pyrazolidinecarboxylic acid

HRID 1396914Notes

Reaction equation

HRID 1396914 reaction equation
[N:1]1([C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21])[CH2:5][CH2:4][CH:3]([C:6]([O:8]C(C)(C)C)=[O:7])[N:2]1C(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O.O>ClCCl>[CH2:23]([O:22][C:20]([N:1]1[CH2:5][CH2:4][CH:3]([C:6]([OH:8])=[O:7])[NH:2]1)=[O:21])[CH:24]=[CH2:25]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 867063572,3-Bis(1,1-dimethylethyl) 1-(2-propen-1-yl) 1,2,3-pyrazolidinetricarboxylate

Product 1

HCID 682879411-[(2-Propen-1-yloxy)carbonyl]-3-pyrazolidinecarboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,3-Bis(1,1-dimethylethyl) 1-(2-propen-1-yl) 1,2,3-pyrazolidinetricarboxylate (1.2 g, 3.37 mmol) was dissolved in dichloromethane (DCM) (6.63 ml) under N2 at ambient temperature. TFA (15.56 ml, 202 mmol) and water (1.820 ml, 101 mmol) were added in one portion. The reaction was stirred at ambient temperature for 3 days. The solvent was removed under reduced pressure to give crude 1-[(2-propen-1-yloxy)carbonyl]-3-pyrazolidinecarboxylic acid (0.674 g, 3.37 mmol, 100% crude yield). MS (ES+) m/z 201.0 (MH+).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a0f779dd189e4988b1cc95625c56a12b
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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