HCID 12114350, compound → HCID 23396152, compound

HRID 967336Notes

Reaction equation

HRID 967336 reaction equation
[N:1]([C@@H:4]1[C@@H:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C@@H:10]([OH:22])[C@@H:9]([CH2:23][O:24][Si:25]([C:38]([CH3:41])([CH3:40])[CH3:39])([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:8][C@H:5]1[S:6][CH3:7])=[N+:2]=[N-:3].[C:42]1([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:43]([C:48](Cl)=[O:49])=[CH:44][CH:45]=[CH:46][CH:47]=1>CN(C)C1C=CN=CC=1.ClCCCl>[N:1]([C@@H:4]1[C@@H:11]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[C@@H:10]([O:22][C:48]([C:43]2[C:42]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:49])[C@@H:9]([CH2:23][O:24][Si:25]([C:38]([CH3:41])([CH3:40])[CH3:39])([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[O:8][C@H:5]1[S:6][CH3:7])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 12114350HCID 12114350, compoundHCID 12563768[1,1'-Biphenyl]-2-carbonyl chloride

Product 1

HCID 23396152HCID 23396152, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A mixture of methyl 2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside (16) (213 mg, 0.36 mmol), 4-dimethylaminopyridine (67 mg, 0.55 mmol) in dry 1,2-dichloroethane (10 mL) was stirred at room temperature. Biphenylcarbonyl chloride (119 mg, 0.55 mmol) was added to the stirred reaction mixture. The resulting suspension was stirred under reflux for 3 hours. The reaction mixture was cooled to 10° C. and filtered. The crystalline solid was washed on the funnel with dry 1,2-dichloroethane (5 mL) and filtered. The filtrates were combined, diluted with CHCl3 (20 mL) and washed twice with diluted brine solution (water-brine 2:1) (15 mL). The organic layer was dried over MgSO4 and evaporated. The residue was purified by chromatography using hexane—CHCl3 1:1 as the mobile phase to give methyl 2-azido-6-O-tert-butyldiphenylsilyl-4-O-biphenylcarbonyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside (17) (18mg, 65%).

Workup

  1. stirringThe resulting suspension was stirred
  2. temperatureunder reflux for 3 hours
  3. temperatureThe reaction mixture was cooled to 10° C.
  4. filtrationfiltered
  5. washThe crystalline solid was washed on the funnel with dry 1,2-dichloroethane (5 mL)
  6. filtrationfiltered
  7. additiondiluted with CHCl3 (20 mL)
  8. washwashed twice with diluted brine solution (water-brine 2:1) (15 mL)
  9. dry with materialThe organic layer was dried over MgSO4
  10. customevaporated
  11. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-e0be0b1e90244c68a7349ee77f85e050
Source dataset
uspto-grants-2005_10
Patent number
US06953850B1

Reaction notes

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