Hydrochloric Acid → HCID 10018324, compound

HRID 892413Notes

Reaction equation

HRID 892413 reaction equation
C[O:2][C:3](=[O:24])[CH:4]([NH2:23])[CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[CH2:16][P:17]([O:21]C)([O:19]C)=[O:18])[N:12]=[CH:11][CH:10]=[N:9]2.COC(=O)CN=CC1C=CC=CC=1.Cl>>[NH2:23][CH:4]([CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[CH2:16][P:17]([OH:19])([OH:21])=[O:18])[N:12]=[CH:11][CH:10]=[N:9]2)[C:3]([OH:24])=[O:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 4169153Methyl [(phenylmethylidene)amino]acetateHCID 9998169HCID 9998169, compound

Product 1

HCID 10018324HCID 10018324, compound

Procedure

The 6,7-bis(bromomethyl)quinoxaline was reacted with trimethyl phosphite to obtain the intermediate dimethyl phosphonate which was converted to α-amino-7-[(dimethoxyphosphinyl)methyl]-6-quinoxalinepropanoic acid methyl ester using N-benzylidene glycine methyl ester. Hydrolysis with 6N hydrochloric acid afforded α-amino-7-(phosphonomethyl)-6-quinoxalinepropanoic acid; m.p. 250° C.; MS (neg. FAB) 310; 1H NMR (DMSO-d6, 1 drop of DCl, 400 MHz): δ3.3-3.6 (overlapping multiplets, 4H, CH2), 4.39 (t, J=6 Hz, 1H, CH), 7.99 (d, J=3.5 Hz, 1H, ArH), 8.03 (s, 1H, ArH), 8.89 (broad s, 2H, H-2 and H-3).

Sources & evidence

ORD record
ord-fe4ee8172ad34be586b1635769f0a9f1
Source dataset
uspto-grants-1992_06
Patent number
US05118675

Reaction notes

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