HCID 66607994, compound → HCID 58242574, compound

HRID 1514456Notes

Reaction equation

HRID 1514456 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH3:15])=[CH:10][CH:9]=2)=[C:5]([CH3:16])[N:4]([C@@H:17]2[O:46][C@H:45]([CH2:47][O:48]CC3C=CC=CC=3)[C@@H:36]([O:37]CC3C=CC=CC=3)[C@H:27]([O:28]CC3C=CC=CC=3)[C@H:18]2[O:19]CC2C=CC=CC=2)[N:3]=1>C(O)C.O1CCCC1.[OH-].[Pd+2].[OH-]>[CH3:1][C:2]1[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH3:15])=[CH:10][CH:9]=2)=[C:5]([CH3:16])[N:4]([C@@H:17]2[O:46][C@H:45]([CH2:47][OH:48])[C@@H:36]([OH:37])[C@H:27]([OH:28])[C@H:18]2[OH:19])[N:3]=1

Participants

5

Reactant 1

HCID 66607994HCID 66607994, compound

Product 1

HCID 58242574HCID 58242574, compoundYield 78.6%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(4-ethylphenylmethyl)-2,4-pentanedione 28 (700 mg) and 2,3,4,6-tetra-O-benzyl-α,β-D-glucosehydrazone 29 (1.70 g) (See Schmidt, R. R. et al., Liebigs Ann. Chem. 1981, 2309) were dissolved in tetrahydrofuran (20 ml), and the mixture was stirred at room temperature for 18 hours under argon atmosphere. The solvent was evaporated under reduced pressure, and the residue was dissolved in toluene (20 ml), and the mixture was heated with stirring under reflux for 2 hours. The mixture was left alone until it was cooled, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10-65:35) to give 3,5-dimethyl-4-(4-ethylphenylmethyl)-1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)pyrazole 30 (299 mg) as a pale yellow semisolid. APCI-Mass m/Z 737 (M+H). (2) The above tetrabenzyl compound 30 (294 mg) was dissolved in a mixture of ethanol (5 ml) and tetrahydrofuran (4 ml), and added thereto was palladium hydroxide (100 mg), and the mixture was stirred at room temperature for 16 hours under hydrogen atmosphere under normal pressure. Insoluble materials were filtered off, and the solvent was evaporated under reduced pressure. The residue was crystallized from diethyl ether to give the desired 3,5-dimethyl-4-(4-ethylphenylmethyl)-1-(β-D-glucopyranosyl)pyrazole 31 (118 mg) as colorless powder. APCI-Mass m/Z 377 (M+H).

Workup

  1. additionadded
  2. filtrationInsoluble materials were filtered off
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-26770d99eed142fdb0d9943d1de8c84a
Source dataset
uspto-grants-2012_07
Patent number
US08222219B2

Reaction notes

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