Triisopropyl phosphite → HCID 53753995, compound

HRID 376134Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:24])[CH:5]([NH:21][CH:22]=[O:23])[CH:6]=[C:7]([CH2:19]Br)[CH2:8][CH2:9][O:10][C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:2].[P:25]([O:34]C(C)C)([O:30][CH:31]([CH3:33])[CH3:32])[O:26][CH:27]([CH3:29])[CH3:28]>>[CH2:1]([O:3][C:4](=[O:24])[CH:5]([NH:21][CH:22]=[O:23])[CH:6]=[C:7]([CH2:19][P:25]([O:30][CH:31]([CH3:33])[CH3:32])([O:26][CH:27]([CH3:29])[CH3:28])=[O:34])[CH2:8][CH2:9][O:10][C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:2]

Participants

Reactant 2

HCID 8304Triisopropyl phosphite

HCID 53666757HCID 53666757, compound

Product 1

HCID 53753995HCID 53753995, compound

Procedure

8.4 g (21 mmol) of 6-benzoyloxy-4-bromomethyl-2-formylamino-hex-3-enoic acid ethyl ester and 23 ml (84 mmol) of triisopropyl phosphite (90%) are heated to 80° C. and stirred under a pressure of ~130 mbar for 18 hours. The excess triisopropyl phosphite is distilled off and the residue is purified by chromatography on silica gel with ethyl acetate. 6-benzoyloxy-4-diisopropylphosphonomethyl-2-formylamino-hex-3-enoic acid ethyl ester is obtained in the form of a brown oil.

Workup

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

Sources & evidence

ORD record: ord-a1d99245574d4f0995999d6d140497f0
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05488140

Reaction notes

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