Trimethyl phosphite → HCID 86745087, compound

HRID 728865Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]1[CH:10]([C:11]([CH2:13][CH2:14][CH3:15])=[CH2:12])[O:9][CH:8]=[N:7]1)=[O:5])[CH3:2].C(OC(=O)C(NC=O)C(O)C(CCC)=C)C.S(Br)(Br)=O.[P:36]([O:41]C)([O:39][CH3:40])[O:37][CH3:38]>>[CH2:1]([O:3][C:4](=[O:5])[CH:6]([NH:7][CH:8]=[O:9])/[CH:10]=[C:11](\[CH2:13][CH2:14][CH3:15])/[CH2:12][P:36]([O:39][CH3:40])([O:37][CH3:38])=[O:41])[CH3:2]

Participants

Reactant 4

HCID 8472Trimethyl phosphite

HCID 68176Thionyl bromide

HCID 21667294HCID 21667294, compound2×

HCID 53930741HCID 53930741, 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-f1bc7050b45a4e40a5d28be628fcec47
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05051413

Reaction notes

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