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

HRID 750890Notes

Reaction equation

HRID 750890 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 hydrazinecarboxylate in 100 mL diethyl ether, 100 mL dichloromethane and 4.83 mL pyridine while being cooled 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 being cooled with an ice bath
  2. filtrationThe precipitated solid is filtered off
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-42dd4dc76cbe49528e3933ee027d2169
Source dataset
uspto-grants-2008_07
Patent number
US07405232B2

Reaction notes

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