Triethyl phosphite → HCID 23181461, compound

HRID 728859Notes

Reaction equation

HRID 728859 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH:5]([NH:11][CH:12]=[O:13])[CH:6](O)[CH:7]=[CH:8][CH3:9])[CH3:2].S(Br)(Br)=O.[P:19]([O:26]CC)([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22]>>[CH2:1]([O:3][C:4](=[O:14])[CH:5]([NH:11][CH:12]=[O:13])/[CH:6]=[CH:7]/[CH:8]([P:19]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:26])[CH3:9])[CH3:2]

Participants

4

Reactant 3

HCID 31215Triethyl phosphiteHCID 68176Thionyl bromideHCID 54049642HCID 54049642, compound

Product 1

HCID 23181461HCID 23181461, compound

Procedure

The starting material is manufactured as follows: Reaction of crotonaldehyde with isocyanoacetic acid ethyl ester in a manner analogous to that described in Example 1 yields 5-(propen-1-yl)-2-oxazoline-4-carboxylic acid ethyl ester. By hydrolysis of the 5-(propen-1-yl)-2-oxazoline-4-carboxylic acid ethyl ester analogously to Example 1, 2-formylamino-3-hydroxy-4-hexenoic acid ethyl ester is obtained. Reaction of the 2-formylamino-3-hydroxy-4-hexenoic acidethyl ester with thionyl bromide and subsequent treatment with triethyl phosphite in a manner analogous to that described in Example 1 (12 hours) yields E-2-formylamino-5-diethylphosphono-5-methyl-3-pentenoic acid ethyl ester.

Workup

  1. customthat described in Example 1 (12 hours)

Sources & evidence

ORD record
ord-b786e209890f445a92293af4a5e04eb3
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

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