Triethylamine → Tert-butyl 2-{[1-(4-bromophenyl)cyclopropyl]carbonyl}hydrazinecarboxylate

HRID 1424004Notes

Reaction equation

HRID 1424004 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.O[N:15]1C2C=CC=CC=2N=[N:16]1.[CH2:24](N(CC)CC)C.Cl.C(N=C=N[CH2:37][CH2:38][CH2:39]N(C)C)C.[C:43](=[O:46])([O-])[OH:44].[Na+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]([NH:15][NH:16][C:43]([O:44][C:38]([CH3:37])([CH3:39])[CH3:24])=[O:46])=[O:13])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 162279661-(4-Bromophenyl)cyclopropane-1-carboxylic acid

Product 1

HCID 86712857Tert-butyl 2-{[1-(4-bromophenyl)cyclopropyl]carbonyl}hydrazinecarboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the compound (25.8 g, 107 mmol) obtained in Example 16-1), 1-hydroxybenzotriazole (15.9 g, 118 mmol), triethylamine (37.4 mL, 268 mol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (22.6 g, 118 mmol), and tert-butoxycarbonylhydrazide (17.0 g, 129 mmol) in N,N-dimethylformamide (500 mL) was stirred at room temperature for 15 h. Saturated aqueous sodium hydrogencarbonate was added to the reaction mixture, and the mixture was extracted with dichloromethane. The organic layer was washed with water and saturated sodium chloride solution in this order and dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was dried under reduced pressure to obtain the title compound (36.2 g, 95%) as a white solid.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with water and saturated sodium chloride solution in this order
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-fd039292808d409eb47b09da4ed3c9eb
Source dataset
uspto-grants-2015_01
Patent number
US08927536B2

Reaction notes

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