Triethyl phosphite → HCID 21667321, compound

HRID 1682310Notes

Reaction equation

HRID 1682310 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH:4]([NH:15][CH:16]=[O:17])[CH:5](O)[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[CH2:7].S(Br)(Br)=O.[P:23]([O:30]CC)([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26]>C(OCC)(=O)C.CCCCCC>[CH3:1][O:2][C:3](=[O:18])[CH:4]([NH:15][CH:16]=[O:17])/[CH:5]=[C:6](\[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)/[CH2:7][P:23]([O:27][CH2:28][CH3:29])([O:24][CH2:25][CH3:26])=[O:30]

Participants

5

Reactant 3

HCID 31215Triethyl phosphiteHCID 68176Thionyl bromideHCID 21667313HCID 21667313, compound

Product 1

HCID 21667321HCID 21667321, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

By reaction of the 2-formylamino-3-hydroxy-4-phenyl-4-pentenoic acid methyl ester with thionyl bromide and subsequent treatment with triethyl phosphite in a manner analogous to that described in Example 1, and after chromatography (silica gel; ethyl acetate/hexane 4:1), E-2-formylamino-4-phenyl-5-diethylphosphono-3-pentenoic acid methyl ester is obtained in the form of a colourless oil. 1H-NMR (CDCl3): 2.98 (d, 2H,C(5)-H); 5.03 (dd, 1H, C(2)-H); 5.77 (dd, 1H, C(3)-H).

Sources & evidence

ORD record
ord-c4f92f8107314c9799494d83be66f483
Source dataset
uspto-grants-1992_12
Patent number
US05175344

Reaction notes

Loading…