methyl (R)-alpha-t-butoxycarbonylamino-6,7-dichloro-3-dimethylphosphonomethyl-2-quinolinepropionate → (R)-alpha-amino-6,7-dichloro-3-(phosphonomethyl)-2-quinolinepropanoic acid

HRID 726647Notes

Reaction equation

HRID 726647 reaction equation
C(OC([NH:8][C@H:9]([CH2:14][C:15]1[C:24]([CH2:25][P:26]([O:30]C)([O:28]C)=[O:27])=[CH:23][C:22]2[C:17](=[CH:18][C:19]([Cl:33])=[C:20]([Cl:32])[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:30])([OH:28])=[O:27])=[CH:23][C:22]2[C:17](=[CH:18][C:19]([Cl:33])=[C:20]([Cl:32])[CH:21]=2)[N:16]=1)[C:10]([OH:12])=[O:11]

Participants

3

Reactant 1

HCID 53893680methyl (R)-alpha-t-butoxycarbonylamino-6,7-dichloro-3-dimethylphosphonomethyl-2-quinolinepropionate

Product 1

HCID 44289458(R)-alpha-amino-6,7-dichloro-3-(phosphonomethyl)-2-quinolinepropanoic acidYield 58%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Methyl (R)-α-t-butoxycarbonylamino-6,7-dichloro-3-dimethylphosphonomethyl-2-quinolinepropionate (0.26 g, 0.5 mmol) was refluxed in 6M HCl (20 ml) for 4 h. The solvent was removed in vacuo and the residue was coevaporated 3 times with acetonitrile. The resulting powder was treated with water and chloroform, filtered off and finally recrystallized from methanol to give 0.11 g of (R)-α-amino-6,7-dichloro-3-(phosphonomethyl)-2-quinolinepropanoic acid. 1H NMR (D2O, 400 MHz): δ 3.15 (d,2H), 3.56 (dd,1H), 3.64 (dd,1H), 4.41 (m,1H), 7.91 (s,1H), 8.00 (s,1H), 8.02 (s,1H).

Workup

  1. customThe solvent was removed in vacuo
  2. additionThe resulting powder was treated with water and chloroform
  3. filtrationfiltered off
  4. customfinally recrystallized from methanol

Sources & evidence

ORD record
ord-32feb1c3610141ff9ee38dfb2bcf093e
Source dataset
uspto-grants-1998_01
Patent number
US05710139

Reaction notes

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