Hydrochloric Acid → HCID 58786102, compound

HRID 1375979Notes

Reaction equation

HRID 1375979 reaction equation
C([O:8][C@@H:9]1[C@@H:14]([O:15]CC2C=CC=CC=2)[C@H:13]([O:23]CC2C=CC=CC=2)[C@@H:12]([CH2:31][O:32]CC2C=CC=CC=2)[O:11][C@H:10]1[C:40]1[CH:45]=[C:44]([O:46][CH3:47])[CH:43]=[C:42]([Br:48])[CH:41]=1)C1C=CC=CC=1.Cl.[H][H]>C1COCC1.CO.[Pd]>[Br:48][C:42]1[CH:41]=[C:40]([C@@H:10]2[O:11][C@H:12]([CH2:31][OH:32])[C@@H:13]([OH:23])[C@H:14]([OH:15])[C@H:9]2[OH:8])[CH:45]=[C:44]([O:46][CH3:47])[CH:43]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 58786138HCID 58786138, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58786102HCID 58786102, compoundYield 58.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

5% palladium/carbon (1.0 g) was added to a solution of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-(3-bromo-5-methoxyphenyl)-D-glucitol (10.0 g) in THF-methanol (ratio: 1:1, 100 ml). Two drops of a 1 M aqueous solution of hydrochloric acid was further added to the mixture, followed by stirring for 30 minutes in a hydrogen atmosphere. After filtrating the reaction mixture, the filtrate was concentrated. The residue was purified by silica gel column chromatography (chloroform-methanol) to obtain (1S)-1,5-anhydro-1-(3-bromo-5-methoxyphenyl)-D-glucitol (2.9 g).

Workup

  1. filtrationAfter filtrating the reaction mixture
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-976e62405cbf4ae0821b358f74718d3f
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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