HCID 66607994, compound → HCID 58242574, compound

HRID 1625724Notes

Reaction equation

HRID 1625724 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

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-384b99ba6f6e4142a757bbcb5b3e8f13
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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