HCID 53731719, compound → HCID 54019952, compound

HRID 1157059Notes

Reaction equation

HRID 1157059 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[OH:13])[CH:5]=[CH:6][C:7](Cl)=[O:8].[C@H:14]1([O:25][C@@H:26]2[C@@H:31]([CH2:32][OH:33])[O:30][C@@H:29]([N:34]=[N+]=[N-])[C@H:28]([OH:37])[C@H:27]2[OH:38])[O:22][C@H:21]([CH2:23][OH:24])[C@@H:19]([OH:20])[C@H:17]([OH:18])[C@H:15]1[OH:16]>CN(C)C=O.N1C=CC=CC=1>[C@H:14]1([O:25][C@@H:26]2[C@@H:31]([CH2:32][OH:33])[O:30][C@@H:29]([NH:34][C:7](=[O:8])[CH:6]=[CH:5][C:4]3[CH:10]=[CH:11][C:12]([OH:13])=[C:2]([OH:1])[CH:3]=3)[C@H:28]([OH:37])[C@H:27]2[OH:38])[O:22][C@H:21]([CH2:23][OH:24])[C@@H:19]([OH:20])[C@H:17]([OH:18])[C@H:15]1[OH:16]

Participants

5

Reactant 2

HCID 53731719HCID 53731719, compoundHCID 53802815HCID 53802815, compound

Product 1

HCID 54019952HCID 54019952, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 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. customat -20° to -15° C.
  2. customat -15° to -5° C.
  3. customfor 20-40 minutes
  4. extractionby extracting with organic solvents

Sources & evidence

ORD record
ord-58b2de3f45384d6081882db7dfe5ee04
Source dataset
uspto-grants-1982_06
Patent number
US04337249

Reaction notes

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