Propylamine → HCID 54055121, compound

HRID 2051795Notes

Reaction equation

HRID 2051795 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].[CH2:13]([NH2:16])[CH2:14][CH3:15].[Cl:17][CH2:18][CH2:19][N:20]=[C:21]=[O:22]>CO.O1CCCC1.C(O)=O>[Cl:17][CH2:18][CH2:19][NH:20][C:21]([N:16]([CH2:13][CH2:14][CH3:15])[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

7

Reactant 3

HCID 7852PropylamineHCID 160352-Chloroethyl isocyanateHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 54055121HCID 54055121, compoundYield 76.6%

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3.6 g of D-glucose, 1.3 g of n-propylamine and 15 ml of methanol is heated at 60° C. for 30 minutes. The reaction mixture is condensed to dryness under reduced pressure and the residue is washed with ether, whereby 4.4 g of 1-n-propylamino-1-deoxy-D-glucose are obtained as a crude product. 4.4 g of said crude product are dissolved in 50 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 room temperature for one hour and the reaction solution is condensed under reduced pressure. The residue thus obtained is dissolved in 20 ml of formic acid and allowed to stand at room temperature for 20 minutes. 200 ml of ether-n-hexane mixture(1:1) is added to the solution and the resultant oily product is washed with ether repeatedly. 5.0 g of 1-(2-chloroethyl)-3-n-propyl-3-D-glucopyranosylurea are thereby obtained as brownish caramel, which can be, if desired, further purified by silica gel chromatography (Solvent: chloroform-ethyl acetate-methanol(1:2:1)) and obtained as colorless caramel.

Workup

  1. customcondensed to dryness under reduced pressure
  2. washthe residue is washed with ether, whereby 4.4 g of 1-n-propylamino-1-deoxy-D-glucose
  3. customare obtained as a crude product
  4. customat 0° to 5° C
  5. customcondensed under reduced pressure
  6. customThe residue thus obtained
  7. waitto stand at room temperature for 20 minutes
  8. washthe resultant oily product is washed with ether repeatedly

Sources & evidence

ORD record
ord-7664fdd0ad634521a53b54cdea67a617
Source dataset
uspto-grants-1980_01
Patent number
US04182757

Reaction notes

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