Citric Acid → HCID 86596739, compound

HRID 916606Notes

Reaction equation

HRID 916606 reaction equation
[C@@H:1]1([O:12][C:13]2[C:18]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)=[C:17]([CH3:28])[CH:16]=[C:15]([CH3:29])[N:14]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].Cl[C:31](OC)=[O:32].C(O)(=O)C[C:37](CC(O)=O)(C(O)=O)[OH:38]>CC1C=C(C)C=C(C)N=1.ClCCl>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][C:18]2[C:13]([O:12][C@@H:1]3[O:9][C@H:8]([C:10](=[C:31]=[O:32])[O:11][O:38][CH3:37])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]3[OH:3])=[N:14][C:15]([CH3:29])=[CH:16][C:17]=2[CH3:28])=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 6586Methyl chloroformateHCID 69015687HCID 69015687, compound

Product 1

HCID 86596739HCID 86596739, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 79532,4,6-TrimethylpyridineSolvent

Procedure

To a solution of 2-(β-D-glucopyranosyloxy)-3-(4-methoxy-benzyl)-4,6-dimethylpyridine (0.32 g) in 2,4,6-trimethyl-pyridine (3.8 mL) was added a solution of methyl chloroformate (0.18 mL) in dichloromethane (0.4 mL) at −40° C. The temperature was raised to room temperature, and the mixture was stirred for 7 hours. To the reaction mixture was added 10% aqueous citric acid solution (12 mL), and the mixture was extracted with ethyl acetate. After the organic layer was washed with 10% aqueous citric acid solution and dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate) to give 3-(4-methoxybenzyl)-2-(6-O-methoxy-carbonyl-β-D-glucopyranosyloxy)-4,6-dimethylpyridine (0.27 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washAfter the organic layer was washed with 10% aqueous citric acid solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-1644bab105244d79a96e786ed40c0c51
Source dataset
uspto-grants-2007_09
Patent number
US07271153B2

Reaction notes

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