Hydrochloric Acid → HCID 59711567, compound

HRID 2222077Notes

Reaction equation

HRID 2222077 reaction equation
[C@@H:1]1([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]#[CH:27])=[CH:22][CH:21]=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:29]([O:31][CH3:32])=[O:30].Cl>N1C(C)=CC(C)=CC=1C>[CH3:32][O:31][C:29]([O:11][CH2:10][C@H:8]1[O:9][C@@H:1]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]#[CH:27])=[CH:24][CH:25]=2)[C@H:2]([OH:3])[C@@H:4]([OH:5])[C@@H:6]1[OH:7])=[O:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 11394605HCID 11394605, compound

Product 1

HCID 59711567HCID 59711567, compound

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

100 mg of 1-(β-D-glucopyranosyloxy)-2-(4-ethynylbenzyl)-benzene in 0.5 ml of 2,4,6-collidine are combined with 0.026 ml of methyl chloroformate in the ice bath and then stirred for 16 hours at ambient temperature. 5 ml of 0.1 N hydrochloric acid are added to the reaction mixture which is then extracted with 10 ml of ethyl acetate. The organic phase is separated off, washed with saturated saline solution and evaporated down. The residue is stirred with 8 ml of diethyl ether/petroleum ether (1:1), the solid is suction filtered and dried at 40° C.

Workup

  1. extractionis then extracted with 10 ml of ethyl acetate
  2. customThe organic phase is separated off
  3. washwashed with saturated saline solution
  4. customevaporated down
  5. stirringThe residue is stirred with 8 ml of diethyl ether/petroleum ether (1:1)
  6. filtrationfiltered
  7. customdried at 40° C.

Sources & evidence

ORD record
ord-1f64a257a76948ee96925864ce047449
Source dataset
uspto-grants-2008_05
Patent number
US07371732B2

Reaction notes

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