Trimethyl phosphite → E-2-formylamino-4-ethyl-5-dimethylphosphono-3-pentenoic acid ethyl ester

HRID 728862Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:15])[CH:5]([NH:12][CH:13]=[O:14])[CH:6](O)[C:7]([CH2:9][CH3:10])=[CH2:8])[CH3:2].S(Br)(Br)=O.[P:20]([O:25]C)([O:23][CH3:24])[O:21][CH3:22]>>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([NH:12][CH:13]=[O:14])/[CH:6]=[C:7](\[CH2:9][CH3:10])/[CH2:8][P:20]([O:23][CH3:24])([O:21][CH3:22])=[O:25])[CH3:2]

Participants

Reactant 3

HCID 8472Trimethyl phosphite

HCID 68176Thionyl bromide

HCID 216672992-Formylamino-3-hydroxy-4-ethyl-4-pentenoic acid ethyl ester

Product 1

HCID 86745086E-2-formylamino-4-ethyl-5-dimethylphosphono-3-pentenoic acid ethyl ester

Procedure

Reaction of the 2-formylamino-3-hydroxy-4-ethyl-4-pentenoic acid ethyl ester with thionyl bromide and subsequent treatment with trimethyl phosphite in a manner analogous to that described in Example 1 yields E-2-formylamino-4-ethyl-5-dimethylphosphono-3-pentenoic acid ethyl ester.

Sources & evidence

ORD record: ord-ca8d0c78b3d14de58fd24e6c5f45449d
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05051413

Reaction notes

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