Trimethyl phosphite → HCID 86745090, compound

HRID 728868Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:16])[CH:5]([NH:13][CH:14]=[O:15])[CH:6](O)[C:7]([CH:9]([CH3:11])[CH3:10])=[CH2:8])[CH3:2].S(Br)(Br)=O.[P:21]([O:26]C)([O:24][CH3:25])[O:22][CH3:23]>>[CH2:1]([O:3][C:4](=[O:16])[CH:5]([NH:13][CH:14]=[O:15])/[CH:6]=[C:7](\[CH:9]([CH3:11])[CH3:10])/[CH2:8][P:21]([O:24][CH3:25])([O:22][CH3:23])=[O:26])[CH3:2]

Participants

Reactant 3

HCID 8472Trimethyl phosphite

HCID 68176Thionyl bromide

HCID 21667298HCID 21667298, compound

Product 1

HCID 86745090HCID 86745090, compound

Procedure

The starting material is manufactured as follows: Reaction of 3-methyl-2-methylene-tutanal 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-c48f746da3ab4be0970d7916b046f444
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05051413

Reaction notes

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