Potassium Fluoride → HCID 66608418, compound

HRID 220998

Reaction equation

HRID 220998 reaction equation
Br[CH2:2][C:3]1[N:4]=[N:5][N:6]([C@@H:8]2[O:25][C@H:24]([CH2:26][O:27][C:28](=[O:30])[CH3:29])[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@H:9]2[O:10][C:11](=[O:13])[CH3:12])[CH:7]=1.C([Sn](CCCC)(CCCC)[C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH3:43])=[CH:38][CH:37]=1)CCC.[F-].[K+]>O1CCCC1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:42]([C:39]1[CH:40]=[CH:41][C:36]([CH2:2][C:3]2[N:4]=[N:5][N:6]([C@@H:8]3[O:25][C@H:24]([CH2:26][O:27][C:28](=[O:30])[CH3:29])[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@H:9]3[O:10][C:11](=[O:13])[CH3:12])[CH:7]=2)=[CH:37][CH:38]=1)[CH3:43]

Participants

7

Reactant 3

HCID 522689Potassium FluorideHCID 60041267Tributyl-(4-ethylphenyl)stannaneHCID 666083074-(bromomethyl)-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-1,2,3-triazole

Product 1

HCID 66608418HCID 66608418, compoundYield 17.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 4-(bromomethyl)-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,2,3-triazole 32 (500 mg) (See Federico G. H. et al., J. Med. Chem. (1979) 29, 496), tri-n-butyl(4-ethylphenyl)tin 33 (604 mg) and tetrakis(triphenylphosphine)palladium (0) (59 mg) in tetrahydrofuran (10 ml) was stirred under heating at 70° C. for 12 hours under argon atmosphere. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and then, an aqueous potassium fluoride solution was added thereto and the mixture was stirred at room temperature for one hour. Insoluble materials were filtered off, and the filtrate was washed with water, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10-50:50) to give 4-(4-ethylphenylmethyl)-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,2,3-triazole 34 (90 mg) as a colorless solid. APCI-Mass m/Z 518 (M+H). (2) From the above tetraacetate compound 34, the desired 4-(4-ethylphenylmethyl)-1-(β-D-glucopyranosyl)1,2,3-triazole 35 was prepared in a manner similar to Example 106-(3) as a colorless solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationInsoluble materials were filtered off
  3. washthe filtrate was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10-50:50)

Sources & evidence

ORD record
ord-cbb99d5359134467ac8861c81d205ae6
Source dataset
uspto-grants-2012_06
Patent number
US08202984B2

Linked notes

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