Triisopropyl phosphite → HCID 53931620, compound

HRID 376118Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:16])[CH:5]([NH:13][CH:14]=[O:15])[CH:6]=[C:7]([CH2:11]Br)[CH2:8][CH2:9][F:10])[CH3:2].[P:17]([O:26]C(C)C)([O:22][CH:23]([CH3:25])[CH3:24])[O:18][CH:19]([CH3:21])[CH3:20]>>[CH2:1]([O:3][C:4](=[O:16])[CH:5]([NH:13][CH:14]=[O:15])[CH:6]=[C:7]([CH2:11][P:17]([O:22][CH:23]([CH3:25])[CH3:24])([O:18][CH:19]([CH3:21])[CH3:20])=[O:26])[CH2:8][CH2:9][F:10])[CH3:2]

Participants

Reactant 2

HCID 8304Triisopropyl phosphite

HCID 54531862HCID 54531862, compound

Product 1

HCID 53931620HCID 53931620, compound

Procedure

1.43 g (4.82 mmol) of 4-bromomethyl-6-fluoro-2-formylamino-hex-3-enoic acid ethyl ester and 5.3 ml (19 mmol) of triisopropyl phosphite (96% ) are heated to 80° and stirred under a pressure of approximately 130 mbar for 18 hours. The excess triisopropyl phosphite is distilled off under reduced pressure and the evaporation residue is purified by chromatography on silica gel with ethyl acetate. 4-diisopropylphosphonomethyl-6-fluoro-2-formylamino-hex-3-enoic acid ethyl ester is obtained in the form of a yellowish oil.

Workup

distillationThe excess triisopropyl phosphite is distilled off under reduced pressure
customthe evaporation residue is purified by chromatography on silica gel with ethyl acetate

Sources & evidence

ORD record: ord-14afa96b77614613a267b63c0b2ce31d
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05488140

Reaction notes

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