Triisopropyl phosphite → HCID 53936186, compound

HRID 487462Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:20])[CH:5]([NH:17][CH:18]=[O:19])[CH:6]=[C:7]([CH2:15]Br)[CH2:8][CH2:9][CH2:10][O:11][C:12](=[O:14])[CH3:13])[CH3:2].[P:21]([O:30]C(C)C)([O:26][CH:27]([CH3:29])[CH3:28])[O:22][CH:23]([CH3:25])[CH3:24]>>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([NH:17][CH:18]=[O:19])[CH:6]=[C:7]([CH2:15][P:21]([O:26][CH:27]([CH3:29])[CH3:28])([O:22][CH:23]([CH3:25])[CH3:24])=[O:30])[CH2:8][CH2:9][CH2:10][O:11][C:12](=[O:14])[CH3:13])[CH3:2]

Participants

Reactant 2

HCID 8304Triisopropyl phosphite

HCID 53734087HCID 53734087, compound

Product 1

HCID 53936186HCID 53936186, compound

Procedure

6.1 g (17.4 mmol) of 7-acetoxy-4-bromomethyl-2-formylaminohept-3-enoic acid ethyl ester and 19.1 ml (69.6 mmol) of triisopropyl phosphite (90%) are heated to 80° C. and stirred under a pressure of approximately 130 mbar for 18 hours. The excess triisopropyl phosphite is distilled off and the residue is purified on silica gel with ethyl acetate. 7-acetoxy-4-diisopropylphosphonomethyl-2-formylamino-hept-3-enoic acid ethyl ester is obtained in the form of a yellow oil.

Workup

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

Sources & evidence

ORD record: ord-992150cb58cd4c2ead97d966e121f5f4
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05294734

Reaction notes

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