Water → methyl 3-[N'-benzyloxycarbonyl-hydrazinocarbonyl)-benzoate

HRID 29803

Reaction equation

HRID 29803 reaction equation
Cl[C:2]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])=[O:3].[NH:14]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[NH2:15].O>C(OCC)C.ClCCl.N1C=CC=CC=1>[CH2:19]([O:18][C:16]([NH:14][NH:15][C:2]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])=[O:3])=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 3

HCID 962WaterHCID 79242Benzyl carbazateHCID 15563901Methyl 3-(chlorocarbonyl)benzoate

Product 1

HCID 12571328methyl 3-[N'-benzyloxycarbonyl-hydrazinocarbonyl)-benzoate

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

10.80 g (54.4 mmol) methyl 3-chlorocarbonyl-benzoate in 100 mL diethyl ether are added dropwise to a solution of 9.04 g (54.4 mmol) benzyl hydrazine carboxylate in 100 mL diethyl ether, 100 mL dichloromethane and 4.83 mL pyridine while cooling with an ice bath. The reaction mixture is stirred overnight at ambient temperature and then combined with water. The precipitated solid is filtered off and washed with diethyl ether. White solid.

Workup

  1. temperaturewhile cooling with an ice bath
  2. filtrationThe precipitated solid is filtered off
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-a1590d231f5e491abba1d3b8bec6d5a0
Source dataset
uspto-grants-2008_09
Patent number
US07423036B2

Linked notes

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