Dimethylformamide → HCID 54019952, compound

HRID 1157056Notes

Reaction equation

HRID 1157056 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:14]([OH:17])(=[O:16])[CH3:15].[C:18]([OH:21])(=O)[CH3:19].[C:22]([OH:25])(=O)[CH3:23].[C:26](O)(=[O:28])C.C(O)(=[O:32])C.C(O)(=O)C.C(O)(=O)C.[C@H]1(O[C@@H:54]2[C@@H](CO)[O:58][C@@H:57]([NH2:62])[C@H:56]([OH:63])[C@H:55]2[OH:64])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O.CN(C)[CH:67]=[O:68]>N1C=CC=CC=1>[C@H:14]1([O:17][C@@H:54]2[C@@H:19]([CH2:18][OH:21])[O:58][C@@H:57]([NH:62][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:56]([OH:63])[C@H:55]2[OH:64])[O:16][C@H:23]([CH2:22][OH:25])[C@@H:67]([OH:68])[C@H:26]([OH:28])[C@H:15]1[OH:32]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 53731719HCID 53731719, compoundHCID 131712763HCID 131712763, compound

Product 1

HCID 54019952HCID 54019952, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3,4-dihydroxycinnamic acid chloride (3) in dimethylformamide at -20° to -15° C. is reacted with 4-O-α-D-glucopyranosyl-β-D-glucopyranosylamine heptaacetate (6) in pyridine at -15° to -5° C. for 30 minutes, then at -5° to +20° C. for 1-2 hours, then extracted with organic solvents, giving N-(4-O-α-D-glucopyranosyl-β-D-glucopyranosyl)-3,4-dihydroxycinnamamide, nonaacetate (nonaester) (7). This nonaacetate (7) is then converted to N-(4-O-α-D-glucopyranosyl-β-D-glucopyranosyl)-3,4-dihydroxycinnamamide (8) by reaction in methanol, triethylamine and water, under an inert atmosphere at ambient temperature for 20-30 hours followed by refluxing for 2-6 hours and extraction in organic solvents. The free sugar derivative (8) is then reacted with triethylamine sulfur trioxide in N,N-dimethylacetamide under an inert atmosphere at 50°-70° C. for 15-20 hours followed by treatment with an alkali or alkaline earth metal acetate in water giving the products (9), where A is the alkali or alkaline earth metal cation.

Workup

  1. extractionextracted with organic solvents

Sources & evidence

ORD record
ord-73cbf436bed640df8848567e17f9f712
Source dataset
uspto-grants-1982_06
Patent number
US04337249

Reaction notes

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