Hydrochloric Acid → HCID 67279155, compound

HRID 1693058Notes

Reaction equation

HRID 1693058 reaction equation
Cl.C([O:5][C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([C@H:13]([NH:15]C(=O)C)[CH3:14])=[CH:8][C:7]=1[O:19][CH3:20])(=O)C>CCO>[ClH:12].[NH2:15][C@@H:13]([C:9]1[C:10]([Cl:12])=[CH:11][C:6]([OH:5])=[C:7]([O:19][CH3:20])[CH:8]=1)[CH3:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67278976HCID 67278976, compound

Product 1

HCID 67279155HCID 67279155, compoundYield 121%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

37% Hydrochloric acid (20 ml) was added to a solution of (R)-4-(1-acetamidoethyl)-5-chloro-2-methoxyphenyl acetate (2.40 g, 8.4 mmol) in EtOH (80 ml) and the mixture was refluxed for 48 hours. The reaction mixture was cooled to room temperature, washed with DCM 3 times, and the aqueous layer was evaporated under reduced pressure. The residue was dissolved in diisopropyl ether and the precipitate was collected by filtration. The solid was washed with DCM and dried in vacuo to give the title compound (1.21 g, 60%) as white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.49 (3H, d, J=6.6 Hz), 3.82 (3H, s), 4.55 (1H, m), 6.91 (1H, s), 7.54 (1H, s), 8.76 (3H, br. s), 9.87 (1H, br. s). MS (ESI) m/z not observed M+ peak.

Workup

  1. temperaturethe mixture was refluxed for 48 hours
  2. washwashed with DCM 3 times
  3. customthe aqueous layer was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in diisopropyl ether
  5. filtrationthe precipitate was collected by filtration
  6. washThe solid was washed with DCM
  7. customdried in vacuo

Sources & evidence

ORD record
ord-6b4a93be0f444affabb4d8f2981ca52b
Source dataset
uspto-grants-2012_04
Patent number
US08158650B2

Reaction notes

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