Ethanol → HCID 70874206, compound

HRID 716097Notes

Reaction equation

HRID 716097 reaction equation
O[CH2:2][C:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])=O.[Cl-].[CH2:14]([NH3+:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)C.O.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:14]([NH:21][CH:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@@H:3]1[NH:33][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 5

HCID 702Ethanol2×HCID 962WaterHCID 5984D-(-)-FructoseHCID 7504BenzylamineHCID 186813287-99-8

Product 1

HCID 70874206HCID 70874206, compound

Procedure

To a mixture of D-(−)-fructose (50 g, 277.5 mmol) in benzyl amine (100 ml) was added benzyl ammonium chloride (30 g, 208 mmol) at room temperature. The mixture was stirred for 6 hours, at which time ethanol (50 ml) was added to make the mixture homogenous. After stirring overnight, another portion of ethanol (50 ml) was added resulting in a homogenous mixture. After 2 hours, water (150 ml) was added and the stirring was continued for 3 hours. The resulting suspension was separated by filtration, and the filtered material was washed with cold aqueous ethanol and dried under vacuum to constant weight, giving 21.3 g of title compound as a white solid. The mother liquor contained N,N′-dibenzyl-1,2-diamino-1,2-dideoxy-D-mannopyranose along with N,N′-dibenzyl-1,2-diamino-1,2-dideoxy-D-glucopyranose.

Workup

  1. additionwas added
  2. customresulting in a homogenous mixture
  3. waitAfter 2 hours
  4. waitthe stirring was continued for 3 hours
  5. customThe resulting suspension was separated by filtration
  6. washthe filtered material was washed with cold aqueous ethanol
  7. customdried under vacuum to constant weight

Sources & evidence

ORD record
ord-85e8125475cf4967b942b2c5a75c9907
Source dataset
uspto-grants-2015_11
Patent number
US09187513B2

Reaction notes

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