Hydrochloric Acid → HCID 57159278, compound

HRID 1532036Notes

Reaction equation

HRID 1532036 reaction equation
[NH2:1][CH:2]([CH2:6][C:7]1[C:8]([O:15][CH2:16][CH3:17])=[N:9][O:10][C:11]=1[C:12]([OH:14])=[O:13])[C:3]([OH:5])=[O:4].Cl.[CH2:19](O)[CH3:20]>>[NH2:1][CH:2]([CH2:6][C:7]1[C:8]([O:15][CH2:16][CH3:17])=[N:9][O:10][C:11]=1[C:12]([OH:14])=[O:13])[C:3]([O:5][CH2:19][CH3:20])=[O:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 10466977HCID 10466977, compound

Product 1

HCID 57159278HCID 57159278, compound

Procedure

A mixture of (RS)-2-amino-3-(5-carboxy-3-ethoxyisoxazol-4-yl)propionic acid (2.0 g, 8.2 mmol) and a solution of HCl in ethanol (35 mL) was boiled under reflux for 3 h to give ethyl (RS)-2-amino-3-(5-carboxy-3-ethoxyisoxazol-4-yl)propionate. Ethyl (RS)-2-Amino-3-(5-carboxy-3-ethoxyisoxazol-4-yl)propionate (0.6 g) was added a dilute solution of NaOH, and the aqueous phase was extracted with ethyl acetate. The organic extracts were washed with brine, dried (MgSO4), filtered and evaporated to dryness in vacuo. The residue was dissolved in acetone (6 mL) and added a solution of oxalic acid (0.14 g, 1.6 mmol) in acetone (6 mL), and the formed precipitate was collected by filtration (110 mg, 10%): mp 159-161° C.; 1H NMR (DMSO-d6) δ1.11 (t, 3 H), 1.32 (t, 3 H), 1.36 (t, 3 H), 3.02 (dd, 1 H), 3.11 (dd, 1 H), 3.98-4.16 (m, 3 H) 4.32 (q, 2 H), 4.37 (q, 2 H); MS ((M+H)+) m/z 301. Anal. calcd, C, 46.15; H, 5.69; N, 7.18; found, C, 46.38; H, 5.69; N, 7.36.

Workup

  1. temperatureunder reflux for 3 h

Sources & evidence

ORD record
ord-c28fa4a59bca468eb4d65fd63023dfaf
Source dataset
uspto-grants-2001_03
Patent number
US06200999B1

Reaction notes

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