Water → 1-(Benzyloxy carbonyl)pyrazolidine-3-carboxylic acid

HRID 1396895Notes

Reaction equation

[N:1]1([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[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>[C:24]1([CH2:23][O:22][C:20]([N:1]2[CH2:5][CH2:4][CH:3]([C:6]([OH:8])=[O:7])[NH:2]2)=[O:21])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 25 °C

Procedure

1-Benzyl 2,3-di-tert-butyl pyrazolidine-1,2,3-tricarboxylate (14.15 g, 34.8 mmol) was dissolved in dichloromethane (68.6 ml) under N2 at room temperature. TFA (80 ml, 1045 mmol) and water (9.41 ml, 522 mmol) were then added in one portion. The reaction was stirred at 25° C. for 2 days. The solvent was then removed under reduced pressure to give 1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid (8.72 g, 34.8 mmol, 100% yield).

Workup

customThe solvent was then removed under reduced pressure

Sources & evidence

ORD record: ord-ec0edc0be2da4b2c8af09051558083bf
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901119B2

Reaction notes

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