Trimethyl phosphite → HCID 86745087, compound

HRID 1682297Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:16])[CH:5]([NH:13][CH:14]=[O:15])[CH:6](O)[C:7]([CH2:9][CH2:10][CH3:11])=[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](\[CH2:9][CH2:10][CH3:11])/[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 21667294HCID 21667294, compound

Product 1

HCID 86745087HCID 86745087, compound

Procedure

The starting material is manufactured as follows: Reaction of 2-methylene-pentanal with isocyanoacetic acid ethyl ester analogously to Example 1 yields 5-(penten-2-yl)-2-oxazoline-4-carboxylic acid ethyl ester. By hydrolysis of the 5-(penten-2-yl)-2-oxazoline-4-carboxylic acid ethyl ester in a manner analogous to that described in Example 15, 2-formylamino- 3-hydroxy-4-propyl-4-pentenoic acid ethyl ester is obtained. Reaction of the 2-formylamino-3-hydroxy-4-propyl-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-propyl-5-dimethylphosphono-3-pentenoic acid ethyl ester.

Sources & evidence

ORD record: ord-2026645f0ecb45c8875cdea76b19dca7
Source dataset: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05175344

Reaction notes

Loading…