Ethyl Acetate → HCID 54470639, compound

HRID 2051789Notes

Reaction equation

HRID 2051789 reaction equation
O=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[CH3:13][NH2:14].CO.[Cl:17][CH2:18][CH2:19][N:20]=[C:21]=[O:22].C(OCC)(=O)C>CO.O1CCCC1.CCOCC>[Cl:17][CH2:18][CH2:19][NH:20][C:21]([N:14]([CH3:13])[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[OH:4])=[O:22]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 160352-Chloroethyl isocyanateHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 57454252Monomethylamine methanol

Product 1

HCID 54470639HCID 54470639, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3.6 g of D-glucose and a 10% methylamine-methanol solution is heated at 60° C. for 20 minutes in a sealed tube. The reaction mixture is condensed to dryness under reduced pressure, whereby 3.8 g of 1-methylamino-1-deoxy-D-glucose are obtained as a crude product. 3.8 g of said crude product are dissolved in 40 ml of methanol, and a solution of 2.5 g of 2-chloroethyl isocyanate in 10 ml of tetrahydrofuran is added dropwise thereto at 0° to 5° C. The solution is stirred at the same temperature for 1.5 hours. Then, the reaction solution is condensed under reduced pressure, and a mixture of ethyl acetate and ether is added to the residue. 4.5 g of 1-(2-chloroethyl)-3-methyl-3-D-glucopyranosylurea are thereby obtained as colorless caramel.

Workup

  1. customare obtained as a crude product
  2. customat 0° to 5° C
  3. customcondensed under reduced pressure
  4. additionis added to the residue

Sources & evidence

ORD record
ord-cc08a78077bc4c00b580c1a2433f77d2
Source dataset
uspto-grants-1980_01
Patent number
US04182757

Reaction notes

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