HCID 53793415, compound → HCID 19706716, compound

HRID 726640Notes

Reaction equation

HRID 726640 reaction equation
C[O:2][C:3](=[O:30])[CH:4]([NH2:29])[CH2:5][C:6]1[C:15]([CH2:16][P:17]([O:22]CC)([O:19]CC)=[O:18])=[CH:14][C:13]2[C:8](=[CH:9][C:10]([O:27][CH3:28])=[C:11]([O:25][CH3:26])[CH:12]=2)[N:7]=1>Cl>[NH2:29][CH:4]([CH2:5][C:6]1[C:15]([CH2:16][P:17]([OH:19])([OH:22])=[O:18])=[CH:14][C:13]2[C:8](=[CH:9][C:10]([O:27][CH3:28])=[C:11]([O:25][CH3:26])[CH:12]=2)[N:7]=1)[C:3]([OH:30])=[O:2]

Participants

3

Reactant 1

HCID 53793415HCID 53793415, compound

Product 1

HCID 19706716HCID 19706716, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

α-Amino-3-(diethylphosphonomethyl)-6,7-dimethoxy-2-quinolinepropanoic acid methyl ester (0.09 g, 0.2 mmol) was refluxed in 6M HCl (15 ml) for 6 h. The mixture was concentrated and dissolved in water. After removal of some undissolved material by filtration, 38 mg of the title compound, α-amino-6,7-dimethoxy-3-(phosphonomethyl)-2-quinolinepropanoic acid was precipitated by addition of acetonitrile. 1H NMR(D2O, 400 MHz: δ 3.22 (dd, 2H), 3.66 (m, 2H), 3.90 (s, 3H), 3.92 (s, 3H), 4.15 (m, 1H), 7.22 (s, 1H), 7.37 (s, 1H), 8.53 (s, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in water
  3. customAfter removal of some undissolved material
  4. filtrationby filtration, 38 mg of the title compound, α-amino-6,7-dimethoxy-3-(phosphonomethyl)-2-quinolinepropanoic acid
  5. customwas precipitated by addition of acetonitrile

Sources & evidence

ORD record
ord-ab8493360d304907b0eb9fa78b19694c
Source dataset
uspto-grants-1998_01
Patent number
US05710139

Reaction notes

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