HCID 10501146, compound → HCID 70007669, compound

HRID 1532023Notes

Reaction equation

HRID 1532023 reaction equation
C([NH:4][C:5](C(OCC)=O)([CH2:11][C:12]1[C:13]([O:22][CH3:23])=[N:14][O:15][C:16]=1[C:17]([O:19]CC)=[O:18])[C:6]([O:8]CC)=[O:7])(=[O:3])C>Cl>[OH2:3].[NH2:4][CH:5]([CH2:11][C:12]1[C:13]([O:22][CH3:23])=[N:14][O:15][C:16]=1[C:17]([OH:19])=[O:18])[C:6]([OH:8])=[O:7]

Participants

3

Reactant 1

HCID 10501146HCID 10501146, compound

Product 1

HCID 70007669HCID 70007669, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of ethyl 2-acetamido-2-(ethoxycarbonyl)-3-[5-(ethoxycarbonyl)-3-methoxyisoxazol-4-yl]propionate (1.2 g, 3.0 mmol) in 0.5 M HCl (100 mL) was boiled under reflux for 48 h. The mixture was cooled, washed with dichloromethane (100 mL) and diethyl ether (2×100 mL), filtered and concentrated in vacuo. Water was added (5 mL) and the pH adjusted to about 3 by addition of NaOH (0.1 M and 1 M). The aqueous phase was reduced in vacuo (2 mL) and a precipitate collected by filtration. The precipitate was stirred in water (2 mL) at room temperature for 24 h affording Comp. 1 after filtration (70 mg, 10%): mp 222-225° C. (dec); 1H NMR (DMSO-d6) δ2.88 (dd, 1 H), 3.01 (dd, 1 H), 3.85-3.96 (m, 1 H), 3.90 (s, 3 H); 13C NMR (DMSO-d6) d 22.70, 52.38, 57.32, 103.25, 159.43, 165.95, 170.66 (2 C); MS ((M+H)+) m/z 231. Anal. (C8H10N2O6.0.25H2O) calcd, C, 40.94; H, 4.51; N, 11.94; found, C, 41.01; H, 4.37; N, 11.91.

Workup

  1. temperatureunder reflux for 48 h
  2. temperatureThe mixture was cooled
  3. washwashed with dichloromethane (100 mL) and diethyl ether (2×100 mL)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. additionWater was added (5 mL)
  7. additionthe pH adjusted to about 3 by addition of NaOH (0.1 M and 1 M)
  8. filtrationa precipitate collected by filtration
  9. customaffording Comp
  10. filtration1 after filtration (70 mg, 10%)

Sources & evidence

ORD record
ord-1fca170257e5489e97c6ccf1dab1bd2d
Source dataset
uspto-grants-2001_03
Patent number
US06200999B1

Reaction notes

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