Thionyl Chloride → HCID 53802815, compound

HRID 1157058Notes

Reaction equation

HRID 1157058 reaction equation
OC1C=C(C=CC=1O)C=CC(Cl)=O.S(Cl)(Cl)=O.[C@H:18]1([O:29][C@@H:30]2[C@@H:35]([CH2:36][OH:37])[O:34][C@@H:33](Br)[C@H:32]([OH:39])[C@H:31]2[OH:40])[O:26][C@H:25]([CH2:27][OH:28])[C@@H:23]([OH:24])[C@H:21]([OH:22])[C@H:19]1[OH:20].[N-:41]=[N+:42]=[N-:43].[Na+]>CN(C)C=O.CS(C)=O>[C@H:18]1([O:29][C@@H:30]2[C@@H:35]([CH2:36][OH:37])[O:34][C@@H:33]([N:41]=[N+:42]=[N-:43])[C@H:32]([OH:39])[C@H:31]2[OH:40])[O:26][C@H:25]([CH2:27][OH:28])[C@@H:23]([OH:24])[C@H:21]([OH:22])[C@H:19]1[OH:20]

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 53731719HCID 53731719, compoundHCID 54203883HCID 54203883, compound

Product 1

HCID 53802815HCID 53802815, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

A method for producing compounds of the formula: ##STR8## wherein A is selected from the group consisting of alkali metal cations and alkaline earth metal cations which comprises reacting 3,4-dihydroxycinnamic acid with acetic anhydride in pyridine for 18-30 hours, in organic solvents, giving 3,4-dihydroxycinnamic acid, diacetate, then converting to 3,4-dihydroxycinnamic acid chloride by treating with thionyl chloride in dimethylformamide at -20° to -18° C. for 30-90 minutes; reacting 4-O-α-D-glucopyranosyl-β-D-glucopyranosyl bromide, heptaacetate with sodium azide in dimethylsulfoxide at 55°-65° C. for 10-30 minutes, extracting in organic solvents, giving 4-O-α-D-glucopyranosyl-β-D-glucopyranosylazide, heptaacetate, then catalytically reducing, giving 4-Oα-D-glucopyranosyl-β-D-glucopyranosylamine, heptaacetate (heptaester); reacting a solution of the 3,4-dihydroxycinnamic acid chloride in dimethylformamide at -20° to -15° C. with a solution of the 4-O-α-D-glucopyranosyl-β-D-glucopyranosylamine, heptaacetate in pyridine at -15° to -5° C. for 20-40 minutes, then at -5° to 20° C. for 1-2 hours followed by extracting with organic solvents, giving N-(4-O-α-D-glucopyranosyl-β-D-glucopyranosyl)-3,4-dihydroxycinnamamide, nonaacetate (nonaester), then converting to N-(4-O-α-D-glucopyranosyl-β-D-glucopyranosyl)-3,4-dihydroxycinnamamide by reacting in a mixture of methanol, triethylamine and water, under an inert atmosphere for 20-30 hours followed by heating at reflux for 2-6 hours and extracting in organic solvents, reacting this derivative with triethylamine sulfur trioxide in N,N-dimethylacetamide under an inert atmosphere at 50°-70° C. for 15-20 hours, and then treating with an alkali metal or alkaline earth metal acetate in water.

Workup

  1. extractionextracting in organic solvents

Sources & evidence

ORD record
ord-45c1dc82ef754b44888f9928d5e4e741
Source dataset
uspto-grants-1982_06
Patent number
US04337249

Reaction notes

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