Hydrochloric Acid → HCID 59699472, compound

HRID 2234760Notes

Reaction equation

HRID 2234760 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 899.7%

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 10 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-782f0727c24a4e609d592b9d7bcd687a
Source dataset
uspto-grants-2010_05
Patent number
US07713950B2

Reaction notes

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