Hydrochloric Acid → HCID 59699472, compound

HRID 901080Notes

Reaction equation

HRID 901080 reaction equation
[F:1][CH2:2][C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH2:17][F:18])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[O:6]C(C2C=CC=CC=2)=[N:4]1.Cl.C(OCC)(=O)C>ClCCl>[NH2:4][C@H:3]([CH2:2][F:1])[C@@H:7]([C:8]1[CH:9]=[CH:10][C:11]([S:14]([CH2:17][F:18])(=[O:16])=[O:15])=[CH:12][CH:13]=1)[OH:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 59699476HCID 59699476, compound

Product 1

HCID 59699472HCID 59699472, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of sulfone 22 (1.47 g, 4.19 mmol) in dichloromethane (50 mL) was mixed with 6N HCl (40 mL). Dichloromethane was distilled out and the resulting white suspension was stirred at reflux for 14 hours. It was cooled to room temperature and treated with aqueous NaHCO3 to pH=8˜9. Extraction with dichloromethane (3×50 mL) afforded an oil residue which was subjected to flash chromatography (SiO2, hexanes/ethyl acetate=2:1 to ethyl acetate 100%) to provide 1.0 g of the desired product, as a light yellow oil. 1H NMR (400 MHz, CDCl3) 3.05-3.15 (m, 1H), 4.24-4.52 (m, 2H), 4.72 (d, J=6 Hz, 1H), 5.09 (s, 1H), 5.21 (s, 1H), 7.62 (d, J=9 Hz, 2H), 7.93 (d, J=9 Hz, 2H).

Workup

  1. distillationDichloromethane was distilled out
  2. temperatureat reflux for 14 hours
  3. additiontreated with aqueous NaHCO3 to pH=8˜9
  4. extractionExtraction with dichloromethane (3×50 mL)
  5. customafforded an oil residue which

Sources & evidence

ORD record
ord-77a2215e9b4a44f69438d3bf5ce924be
Source dataset
uspto-grants-2008_04
Patent number
US07361689B2

Reaction notes

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