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

HRID 463915Notes

Reaction equation

HRID 463915 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-0cf64b77897c44cb9b4a7e9fc65da854
Source dataset
uspto-grants-1985_10
Patent number
US04544751

Reaction notes

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