HCID 12114344, compound → HCID 23396150, compound

HRID 967334Notes

Reaction equation

HRID 967334 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 12114344HCID 12114344, compoundHCID 12563768[1,1'-Biphenyl]-2-carbonyl chloride

Product 1

HCID 23396150HCID 23396150, compoundYield 76.5%

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 glucopyranoside (10) (12.7 g, 21.46 mmol), 4-dimethylaminopyridine (5.23 g, 42.92 mmol) in dry 1,2-dichloroethane (100 mL) was stirred at room temperature. Biphenylcarbonyl chloride (6.97 g, 32.19 mmol) was added to the stirred reaction mixture in 15 minutes. After the addition 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 (50 mL) and filtered. The filtrates were combined, diluted with CHCl3 (200 mL) and washed twice with diluted brine solution (water-brine 2:1) (150 mL). The organic layer was dried over MgSO4 and evaporated. The residue was crystallized from EtOH (75 mL) to give methyl 2-azido-6-O-tert-butyldiphenylsilyl-4-O-biphenylcarbonyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (11) (12.7 g, 76%)

Workup

  1. additionAfter the addition the resulting suspension
  2. stirringwas stirred
  3. temperatureunder reflux for 3 hours
  4. temperatureThe reaction mixture was cooled to 10° C.
  5. filtrationfiltered
  6. washThe crystalline solid was washed on the funnel with dry 1,2-dichloroethane (50 mL)
  7. filtrationfiltered
  8. additiondiluted with CHCl3 (200 mL)
  9. washwashed twice with diluted brine solution (water-brine 2:1) (150 mL)
  10. dry with materialThe organic layer was dried over MgSO4
  11. customevaporated
  12. customThe residue was crystallized from EtOH (75 mL)

Sources & evidence

ORD record
ord-ca748dcec676446b9186443b3604d021
Source dataset
uspto-grants-2005_10
Patent number
US06953850B1

Reaction notes

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