HCID 54189282, compound → HCID 44289198, compound

HRID 726633Notes

Reaction equation

HRID 726633 reaction equation
C(OC([NH:8][C@H:9]([CH2:14][C:15]1[C:24]([CH2:25][P:26]([O:31]CC)([O:28]CC)=[O:27])=[CH:23][C:22]2[C:17](=[CH:18][C:19]([Cl:34])=[CH:20][CH:21]=2)[N:16]=1)[C:10]([O:12]C)=[O:11])=O)(C)(C)C>Cl>[NH2:8][C@H:9]([CH2:14][C:15]1[C:24]([CH2:25][P:26]([OH:31])([OH:28])=[O:27])=[CH:23][C:22]2[C:17](=[CH:18][C:19]([Cl:34])=[CH:20][CH:21]=2)[N:16]=1)[C:10]([OH:12])=[O:11]

Participants

3

Reactant 1

HCID 54189282HCID 54189282, compound

Product 1

HCID 44289198HCID 44289198, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Methyl(R)-α-t-butoxycarbonylamino-7-chloro-3-diethylphosphonomethyl-2-quinolinepropionate (0.23 g, 0.45 mmol), prepared as described in example 5, was refluxed in 6N hydrochloric acid (10 ml) for 6 hours. The mixture was concentrated in vacuo and 100 mg of (R)-α-amino-7-chloro-3-(phosphonomethyl)-2-quinolinepropanoic acid was precipitated from water. 1H NMR(D2O, 400 MHz): δ 3.18 (d, 2H, CH2 --P), 3.58 (m, 2H, CH2), 4.38 (m, 1H, CH), 7.12 (d, 1H, ArH), 7.47 (d, 1H, ArH), 7.53 (s, 1H, ArH), 8.42 (d, 1H, ArH).

Workup

  1. concentrationThe mixture was concentrated in vacuo and 100 mg of (R)-α-amino-7-chloro-3-(phosphonomethyl)-2-quinolinepropanoic acid
  2. customwas precipitated from water

Sources & evidence

ORD record
ord-a82ccaf0e1214c88a16fef443e3117eb
Source dataset
uspto-grants-1998_01
Patent number
US05710139

Reaction notes

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