Hydrochloric Acid → HCID 87455623, compound

HRID 1868157Notes

Reaction equation

HRID 1868157 reaction equation
[C:1]([O:9][C:10]([N:12]1[CH2:21][C@@H:18]2[C@H:19]([OH:20])[C@H:13]1[C@H:14]([O:17]2)[O:15][CH3:16])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl>C(Cl)Cl>[C:28]([O:20][C@H:19]1[C@H:18]2[CH2:21][N:12]([C:10]([O:9][C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:11])[C@@H:13]1[C@H:14]([O:17]2)[O:15][CH3:16])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7412Benzoyl chlorideHCID 87455744HCID 87455744, compound

Product 1

HCID 87455623HCID 87455623, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl N-benzoyloxycarbonyl-2,5-dideoxy-2,5-imino-α-D-lyxofuranoside (Tetrahedron, 1986, vol. 42, p. 5685-5692) (13.9 g, 49.8 mmol) was dissolved in methylene chloride (200 mL) and pyridine (20 mL, 249.0 mmol) and benzoyl chloride (11.6 mL, 99.6 mmol) were added thereto, followed by stirring of the mixture at room temperature for 2 hours. After 1N hydrochloric acid (200 mL) was added to the reaction mixture at 0° C. and the mixture was extracted with methylene chloride (100 mL), the organic layer was washed with saturated aqueous sodium hydrogencarbonate (200 mL) and saturated brine (200 mL) and dried with anhydrous sodium sulfate, followed by distilling off of the solvent under reduced pressure. The residue was purified using silica gel flash column chromatography (hexane:ethyl acetate, 5:1-3:1, V/V) to obtain the desired title compound (15.82 g, yield 83%) as a colorless solid.

Workup

  1. extractionthe mixture was extracted with methylene chloride (100 mL)
  2. washthe organic layer was washed with saturated aqueous sodium hydrogencarbonate (200 mL) and saturated brine (200 mL)
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationby distilling off of the solvent under reduced pressure
  5. customThe residue was purified

Sources & evidence

ORD record
ord-1642e675eb6c41b49e6dbd5b0afe9d47
Source dataset
uspto-grants-2009_12
Patent number
US07632930B2

Reaction notes

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