Triethyl phosphite → HCID 86745092, compound

HRID 728873Notes

Reaction equation

HRID 728873 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5]([NH:17][CH:18]=[O:19])[C:6](O)=[C:7]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:8])[CH3:2].S(Br)(Br)=O.[P:25]([O:32]CC)([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28]>C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([NH:17][CH:18]=[O:19])/[CH:6]=[C:7](\[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)/[CH2:8][P:25]([O:29][CH2:30][CH3:31])([O:26][CH2:27][CH3:28])=[O:32])[CH3:2]

Participants

5

Reactant 3

HCID 31215Triethyl phosphiteHCID 68176Thionyl bromideHCID 86745093HCID 86745093, compound

Product 1

HCID 86745092HCID 86745092, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

By reaction of 2-formylamino-3-hydroxy-4-benzyl-3-pentenoic acid ethyl ester with thionyl bromide and subsequent treatment with triethyl phosphite at 100° in a manner analogous to that described in Example 1, and after chromatography (silica gel; ethyl acetate), E-2-formylamino-4-benzyl-5-diethylphosphono-3-pentenoic acid ethyl ester is obtained in the form of a colourless oil, 1H-NMR (CDCl3): 2.45 (d, 2H, C(5)--H); 3.80 (s, 1H, CH2); 5.51 (m, 1H, C(3)--H).

Sources & evidence

ORD record
ord-4099504d247147e19bd9e015ddb4fa50
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

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