Methanol → HCID 91513383, compound

HRID 967342Notes

Reaction equation

HRID 967342 reaction equation
[H-].[Na+].[N:3]([C@@H:6]1[C@@H:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C@H:12]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:11]([CH2:32][OH:33])[O:10][C@H:7]1[S:8][CH3:9])=[N+:4]=[N-:5].[Cl:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39]Cl)=[CH:37][CH:36]=1.CO>CN(C=O)C>[N:3]([C@@H:6]1[C@@H:13]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[C@H:12]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C@@H:11]([CH2:32][O:33][CH2:39][C:38]2[CH:41]=[CH:42][C:35]([Cl:34])=[CH:36][CH:37]=2)[O:10][C@H:7]1[S:8][CH3:9])=[N+:4]=[N-:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 91272540HCID 91272540, compound

Product 1

HCID 91513383HCID 91513383, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of sodium hydride (71 mg, 1.8 mmol) in dry DMF (5 mL) was cooled to 0° C., and a solution of methyl 2-azido-4-O-benzyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (33) (680 mg, 1.5 mmol) in dry DMF (5 mL) was added dropwise in 30 minutes. The resulting solution was stirred at room temperature for 30 minutes and 4-chlorobenzyl chloride (295 mg, 1.5 mmol) was added dropwise at 0° C. The reaction mixture was stirred at room temperature for 4.5 hours, cooled at 0° C. and dry methanol (1 mL) was added dropwise. The reaction mixture was concentrated under reduced pressure, then xylene (10 mL) was co-evaporated from the residue. The residue was treated with hexane (10 mL) and filtered to give methyl 2-azido-4-O-benzyl-6-O-(4-chlorobenzyl)-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (34) (620 mg, 71%).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 4.5 hours
  2. temperaturecooled at 0° C.
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionThe residue was treated with hexane (10 mL)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-adadd1e99787477d8667c5cafee65025
Source dataset
uspto-grants-2005_10
Patent number
US06953850B1

Reaction notes

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