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

HRID 1284661Notes

Reaction equation

HRID 1284661 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. customto precipitate crystals
  2. filtrationThe crystals were collected by filtration
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-d01fede910c24eda846b3246122a0390
Source dataset
uspto-grants-1986_01
Patent number
US04563522

Reaction notes

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