Ethyl (2Z)-2-methoxyimino-3-oxo-butanoate → Ethyl 2-methoxyimino-3-t-butoxycarbonylhydrazonobutyrate

HRID 364448Notes

Reaction equation

HRID 364448 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:10]([CH3:12])=O)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:13]([O:17][C:18]([NH:20][NH2:21])=[O:19])([CH3:16])([CH3:15])[CH3:14]>C(O)C>[CH3:1][O:2][N:3]=[C:4]([C:10](=[N:21][NH:20][C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[CH3:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 43493Ethyl (2Z)-2-methoxyimino-3-oxo-butanoateHCID 70091tert-Butyl carbazate

Product 1

HCID 54569379Ethyl 2-methoxyimino-3-t-butoxycarbonylhydrazonobutyrate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-methoxyiminoacetoacetate (a mixture of syn and anti isomers) (34.6 g.) and t-butoxycarbonylhydrazine (26.4 g.) in ethanol (200 ml.) was stirred for 7.5 hours at ambient temperature and allowed to stand overnight to precipitate crystals. The crystals were collected by filtration, washed with ethanol and dried to give ethyl 2-methoxyimino-3-t-butoxycarbonylhydrazonobutyrate (a mixture of syn and anti isomers) (41.7 g.), mp 144° to 145° C.

Workup

  1. waitto stand overnight
  2. customto precipitate crystals
  3. filtrationThe crystals were collected by filtration
  4. washwashed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-60f08f63b5ad474cbf2ec565976360fb
Source dataset
uspto-grants-1986_08
Patent number
US04604456

Reaction notes

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