Hydrochloric Acid → HCID 10709759, compound

HRID 1532033Notes

Reaction equation

HRID 1532033 reaction equation
C(OC([NH:8][CH:9]([CH2:15][C:16]1[C:17]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:18][O:19][C:20]=1[C:21]([O:23]CC)=[O:22])[C:10]([O:12]CC)=[O:11])=O)(C)(C)C.Cl>[OH-].[Na+]>[NH2:8][CH:9]([CH2:15][C:16]1[C:17]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:18][O:19][C:20]=1[C:21]([OH:23])=[O:22])[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10813914HCID 10813914, compound

Product 1

HCID 10709759HCID 10709759, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of ethyl (RS)-2-[(tert-butoxycarbonyl)amino]-3-[3-benzyloxy-5-(ethoxycarbonyl)isoxazol-4-yl]propionate (0.65 mg, 1.4 mmol) and 1 M NaOH (50 mL) was boiled under reflux for 16 h. The mixture was cooled (5° C.), acidified with dilute aqueous HCl, and concentrated in vacuo. The residue was recrystallized from water to give (RS)-2-amino-3-(3-benzyloxy-5-carboxyisoxazol-4-yl)propionic acid (0.1 g, 23%): mp 209-211° C. (dec); 1H NMR (DMSO-d6) δ2.95 (dd, 1 H), 3.05 (dd, 1 H), 3.99 (t, 1 H), 5.26 (s, 2 H), 7.31-7.52 (m, 5 H); MS ((M+H)+) m/z 307. Anal. calcd, C, 54.89; H, 4.62; N, 9.15; found, C, 54.31; H, 4.56; N, 8.97.

Workup

  1. temperatureunder reflux for 16 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was recrystallized from water

Sources & evidence

ORD record
ord-b372122831df4291a31775f7a85f4658
Source dataset
uspto-grants-2001_03
Patent number
US06200999B1

Reaction notes

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