Water → HCID 131714694, compound

HRID 1981660Notes

Reaction equation

HRID 1981660 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]=[C:5]=[O:6].C(=O)([O-])[O-].[Ba+2].[CH3:12][O:13][CH2:14][CH2:15][CH2:16][NH:17][CH2:18][C@H:19]1[O:29][CH:23]([O:24]CCCC)[C@H:22]([OH:30])[C@@H:21]([OH:31])[C@@H:20]1[OH:32].[OH2:33]>CO>[CH3:12][O:13][CH2:14][CH2:15][CH2:16][N:17]([CH:18]([OH:33])[C@H:19]1[O:29][C@:23]([CH2:18][CH2:19][CH2:20][CH3:21])([OH:24])[C@H:22]([OH:30])[C@@H:21]([OH:31])[C@@H:20]1[OH:32])[C:5](=[O:6])[NH:4][CH2:3][CH2:2][Cl:1]

Participants

6

Reactant 4

HCID 962WaterHCID 10563Barium CarbonateHCID 160352-Chloroethyl isocyanateHCID 53866311HCID 53866311, compound

Product 1

HCID 131714694HCID 131714694, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Chloroethyl isocyanate (1.33 g) and barium carbonate (2.5 g) were added to a solution of n-butyl 6-(3-methoxy-n-propylamino)-6-deoxy-D-glucopyranoside 1/2 sulfate (3.64 g, 10.5 mmol) in a mixture of water (10 ml) and methanol (30 ml) at 0° to 5° C., and the mixture was heated under reflux on a water bath for 1 hour. The reaction mixture was then filtered while hot, to remove the insoluble barium salt. The filtrate was vacuum-concentrated and fractionated by column chromatography (packing: Kiesel gel 60; eluent: chloroform/methanol 10:1) to separate the α- and β-form of products. The objective α- and β-form product fractions were each vacuum-concentrated at 25° C. and crystallized from aqueous isopropanol, giving 1.40 g of 3-(3-methoxy-n-propyl)-3-(n-butyl α-D-glucopyranose-6-yl)-1-(2-chloroethyl)-urea; yield 32.2%, m.p. 103°-105° C., [α]D20 +50.8° (C 1.0, methanol); and 1.32 g of 3-(3-methoxy-n-propyl)-3-(n-butyl β-D-glucopyranose-6-yl)-1-(2-chloroethyl)urea; yield 30.4%, m.p. 109°-111° C., [α]D20 -4.7° (C 1.0, methanol).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux on a water bath for 1 hour
  3. filtrationThe reaction mixture was then filtered while hot,
  4. customto remove the insoluble barium salt
  5. concentrationThe filtrate was vacuum-concentrated and fractionated by column chromatography (packing: Kiesel gel 60; eluent: chloroform/methanol 10:1)
  6. customto separate the α- and β-form of products
  7. concentrationeach vacuum-concentrated at 25° C.
  8. customcrystallized from aqueous isopropanol

Sources & evidence

ORD record
ord-fa8b1c6a08eb4764862b15f938fbaafb
Source dataset
uspto-grants-1986_06
Patent number
US04593090

Reaction notes

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