Hydrochloric Acid → HCID 44289234, compound

HRID 726631Notes

Reaction equation

HRID 726631 reaction equation
C(OC([NH:8][CH: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]([O:34][CH2:35][CH3:36])=[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]([O:34][CH2:35][CH3:36])=[CH:20][CH:21]=2)[N:16]=1)[C:10]([OH:12])=[O:11]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 19706740HCID 19706740, compound

Product 1

HCID 44289234HCID 44289234, compound

Procedure

Deprotection of the amino acid was effected in refluxing 6M HCl for 6 h. Evaporation of the solvent gave a residue which was put onto an acidic ion-exchange resin and eluted with water. Collection of ninhydrin-sensitive fractions and evaporation of solvent gave (R)-α-amino-3-phosphonomethyl-7-ethoxy-2-quinolinepropanoic acid. 13C-NMR (D2O plus NH3 vapours): δ (ppm) 174.7, 158.7, 156.3, 146.3, 138.0, 137.9, 128.6, 122.6, 118.8, 106.2, 64.4, 54.1, 34.2, 34.0, 32.8, 13.9.

Workup

  1. customEvaporation of the solvent
  2. customgave a residue which
  3. washeluted with water
  4. customCollection of ninhydrin-sensitive fractions and evaporation of solvent

Sources & evidence

ORD record
ord-147c4ac678a245188bc2649121eebe3c
Source dataset
uspto-grants-1998_01
Patent number
US05710139

Reaction notes

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