Trimethyl phosphite → HCID 86745091, compound

HRID 728870Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:17])[CH:5]([NH:14][CH:15]=[O:16])[CH:6](O)[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])=[CH2:8])[CH3:2].S(Br)(Br)=O.[P:22]([O:27]C)([O:25][CH3:26])[O:23][CH3:24]>>[CH2:1]([O:3][C:4](=[O:17])[CH:5]([NH:14][CH:15]=[O:16])/[CH:6]=[C:7](\[C:9]([CH3:12])([CH3:11])[CH3:10])/[CH2:8][P:22]([O:25][CH3:26])([O:23][CH3:24])=[O:27])[CH3:2]

Participants

Reactant 3

HCID 8472Trimethyl phosphite

HCID 68176Thionyl bromide

HCID 23181459HCID 23181459, compound

Product 1

HCID 86745091HCID 86745091, compound

Procedure

The starting material is manufactured as follows: Reaction of 3,3-dimethyl-2-methylene-butanal with isocyanoacetic acid ethyl ester in amanner analogous to that described in Example 1 yields 5-(3,3-dimethylbuten-2-yl)-2-oxazoline-4-carboxylic acid ethyl ester, which is hydrolysed analogously to Example 17 to 2-formylamino-3-hydroxy-4-tert.-butyl-4-pentenoic acid ethyl ester. Subsequent reaction with thionyl bromide followed by treatment with trimethyl phosphite analogously to Example 1 yields E-2-formylamino-4-tert.-butyl-5-dimethylphosphono-3-pentenoic acid ethyl ester.

Sources & evidence

ORD record: ord-ac14ab655c2f4f9bb928b5ad4be123fc
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05051413

Reaction notes

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