3-Methyl-2-methylenebutyraldehyde → HCID 54360806, compound

HRID 1682301Notes

Reaction equation

[CH3:1][CH:2]([CH3:7])[C:3](=[CH2:6])[CH:4]=[O:5].[CH2:8]([O:10][C:11](=[O:15])[CH2:12][N+:13]#[C-:14])[CH3:9]>>[CH2:8]([O:10][C:11]([CH:12]1[CH:4]([C:3]([CH:2]([CH3:7])[CH3:1])=[CH2:6])[O:5][CH:14]=[N:13]1)=[O:15])[CH3:9]

Participants

Reactant 2

HCID 781313-Methyl-2-methylenebutyraldehyde

HCID 533707Ethyl isocyanoacetate

Product 1

HCID 54360806HCID 54360806, compound

Procedure

The starting material is manufactured as follows: Reaction of 3-methyl-2-methylene-butanal with isocyanoacetic acid ethyl ester analogously to Example 1 yields 5-(3-methyl-buten-2-yl)-2-oxazoline-4-carboxylic acid ethyl ester, which is hydrolysed analogously to Example 15 to 2-formylamino-3-hydroxy-4-isopropyl-4-pentenoic acid ethyl ester. Subsequent treatment with thionyl bromide followed by reaction with trimethyl phosphite analogously to Example 1 yields E-2-formylamino-4-isopropyl-5-dimethylphosphono-3-pentenoic acid ethyl ester.

Sources & evidence

ORD record: ord-1aef93260bda47a69c455def376b64cb
Source dataset: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05175344

Reaction notes

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