Water → HCID 86632769, compound

HRID 44157Notes

Reaction equation

HRID 44157 reaction equation
[N:1]([C@H:4]1[C@H:11]([OH:12])[C@@H:10]([CH2:13][OH:14])[O:9][CH:6]([O:7][CH3:8])[C@@H:5]1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[N+:2]=[N-:3].[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>N1C=CC=CC=1>[N:1]([C@H:4]1[C@H:11]([OH:12])[C@@H:10]([CH2:13][O:14][C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:9][CH:6]([O:7][CH3:8])[C@@H:5]1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 86632770Methyl 3-azido-2-O-benzyl-3-deoxy-D-glucopyranoside

Product 1

HCID 86632769HCID 86632769, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl 3-azido-2-O-benzyl-3-deoxy-D-glucopyranoside (93 mg) was dissolved in 0.84 mL of pyridine. Benzoyl chloride (45 μL) was added to the solution at −20° C. with stirring, and the mixture was stirred at −20° C. for one hr. Water (14 μL) was added thereto, and the mixture was stirred at −20° C. for 30 min. The contents were concentrated to dryness. Chloroform (10 mL) was added thereto, and the mixture was washed three times with 5 mL of a saturated aqueous sodium bicarbonate solution, three times with 5 mL of a 5% aqueous potassium bisulfate solution and three times with 5 mL of water, was dried over a Glauber's salt and was concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (25 g, hexane:ethyl acetate=3:1) to give the title compound (97 mg, yield 78%).

Workup

  1. stirringthe mixture was stirred at −20° C. for one hr
  2. stirringthe mixture was stirred at −20° C. for 30 min
  3. concentrationThe contents were concentrated to dryness
  4. additionChloroform (10 mL) was added
  5. washthe mixture was washed three times with 5 mL of a saturated aqueous sodium bicarbonate solution, three times with 5 mL of a 5% aqueous potassium bisulfate solution and three times with 5 mL of water
  6. dry with materialwas dried over a Glauber's salt
  7. concentrationwas concentrated under the reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (25 g, hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-7270667668b340f586b8c98e21aa80e4
Source dataset
uspto-grants-2013_09
Patent number
US08541394B2

Reaction notes

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