Acetic Acid → Tert-butyl 2-(1-benzhydrylazetidin-3-ylidene)hydrazinecarboxylate

HRID 1473338Notes

Reaction equation

[CH:1]([N:14]1[CH2:17][C:16](=O)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[NH2:20].C(O)(=O)C>CO>[CH:1]([N:14]1[CH2:17][C:16](=[N:20][NH:19][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

The title compound was prepared as described in WO2010079443A1. To a solution of compound 1-benzhydrylazetidin-3-one (11.7 g, 49.3 mmol) in the methanol (150 mL), tert-butyl hydrazinecarboxylate (6.51 g, 49.3 mmol) was added. Then glacial acetic acid (5.92 mL) was added dropwise at 0° C. The reaction was stirred at 25° C. for 5 h under a nitrogen atmosphere. Then the solvent was evaporated off. The residue was dissolved in dichloromethane (200 mL) and washed with water (2×500 mL). The organic part was dried over sodium sulfate, filtered and concentrated under a vacuum to give the crude tert-butyl 2-(1-benzhydrylazetidin-3-ylidene)hydrazinecarboxylate (16.9 g, 97%) as a white solid. This material was used as is for the next step. MS (ESI, positive ion) m/z (M+1): 352.19.

Workup

customThen the solvent was evaporated off
dissolutionThe residue was dissolved in dichloromethane (200 mL)
washwashed with water (2×500 mL)
dry with materialThe organic part was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under a vacuum

Sources & evidence

ORD record: ord-7feb3dd3843f48b9b6893bf3ecfc538d
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012443B2

Reaction notes

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