Triisopropyl phosphite → HCID 53931620, compound

HRID 487453Notes

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-flouro-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-b989fe87217b401c8728162e0d0ccd4d
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05294734

Reaction notes

Loading…