4-Bromo-2-fluorophenyl isocyanate → 1,1-Dimethylethyl 3-[2-(2-{[(4-bromo-2-fluorophenyl)amino]carbonyl}hydrazino)-2-oxoethyl]-1-azetidinecarboxylate

HRID 2405404Notes

Reaction equation

HRID 2405404 reaction equation
[NH:1]([C:3](=[O:16])[CH2:4][CH:5]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6]1)[NH2:2].[Br:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]=[C:25]=[O:26])=[C:20]([F:27])[CH:19]=1>ClCCl>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:2][NH:1][C:3](=[O:16])[CH2:4][CH:5]2[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:6]2)=[O:26])=[C:20]([F:27])[CH:19]=1

Participants

4

Reactant 2

HCID 27333654-Bromo-2-fluorophenyl isocyanateHCID 67355105Tert-butyl 3-(2-hydrazinyl-2-oxoethyl)azetidine-1-carboxylate

Product 1

HCID 673536431,1-Dimethylethyl 3-[2-(2-{[(4-bromo-2-fluorophenyl)amino]carbonyl}hydrazino)-2-oxoethyl]-1-azetidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round bottom flask under nitrogen, a solution of 1,1-dimethylethyl 3-(2-hydrazino-2-oxoethyl)-1-azetidinecarboxylate (15.18 mmol) in dichloromethane (20 mL) at 0° C. was treated with 4-bromo-2-fluorophenylisocyanate (15.18 mmol). The cooling bath was removed and the clear yellow solution was stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo to afford the crude title compound as a white foamy solid. This material was used directly without further purification. MS(ES)+ m/e 445.2, 447.2 [M+H]+.

Workup

  1. customThe cooling bath was removed
  2. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-ad228275014542208dcf5b058b2ec4a0
Source dataset
uspto-grants-2014_08
Patent number
US08802864B2

Reaction notes

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