Hydrazine → Tert-butyl 3-(tert-butoxycarbonyl(2-hydrazinyl-2-oxoethyl)amino)azetidine-1-carboxylate

HRID 1855184Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH2:20][C:21](OCC)=[O:22])[CH:9]1[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:26][NH2:27]>C(O)C>[C:1]([O:5][C:6]([N:8]([CH2:20][C:21]([NH:26][NH2:27])=[O:22])[CH:9]1[CH2:10][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of tert-butyl 3-(tert-butoxycarbonyl(2-ethoxy-2-oxoethyl)amino)azetidine-1-carboxylate (7.2 g, 20 mmol), hydrazine (5.0 g, 100 mmol) and ethanol (50 mL) was stirred at 80° C. for 17 hrs. The reaction mixture was then concentrated to afford the crude tert-butyl 3-(tert-butoxycarbonyl(2-hydrazinyl-2-oxoethyl)amino)azetidine-1-carboxylate (6.4 g, 94%) as a white solid, which was used directly in the next step. ESI-MS (EI+, m/z): 345.0 [M+H]+.

Workup

concentrationThe reaction mixture was then concentrated

Sources & evidence

ORD record: ord-995da5626b5b42f0956dc6c39ffa834d
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962843B2

Reaction notes

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