Sodium Hydroxide → HCID 69516736, compound

HRID 1351104Notes

Reaction equation

HRID 1351104 reaction equation
[OH:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][C:5]1[C:6](=[O:16])[NH:7][N:8]([CH2:13][CH2:14][OH:15])[C:9]=1[CH:10]([CH3:12])[CH3:11].[CH3:21][C:22]([O:24][CH2:25][C@H:26]1[O:31][C@H:30](Br)[C@H:29]([O:33][C:34]([CH3:36])=[O:35])[C@@H:28]([O:37][C:38]([CH3:40])=[O:39])[C@@H:27]1[O:41][C:42]([CH3:44])=[O:43])=[O:23].[OH-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.ClCCl>[OH:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][C:5]1[C:6]([O:16][C@@H:30]2[O:31][C@H:26]([CH2:25][O:24][C:22](=[O:23])[CH3:21])[C@@H:27]([O:41][C:42](=[O:43])[CH3:44])[C@H:28]([O:37][C:38](=[O:39])[CH3:40])[C@H:29]2[O:33][C:34](=[O:35])[CH3:36])=[N:7][N:8]([CH2:13][CH2:14][OH:15])[C:9]=1[CH:10]([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 101776alpha-D-Glucopyranosyl bromide, tetraacetateHCID 22932161HCID 22932161, compound

Product 1

HCID 69516736HCID 69516736, compoundYield 17.7%

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-hydroxybenzyl)-1-(2-hydroxyethyl)-5-isopropyl-1,2-dihydropyrazol-3-one (90 mg), acetobromo-α-D-glucose (161 mg) and benzyl tri(n-butyl)ammonium chloride (101 mg) in dichloromethane (5 mL) was added 2 mol/L aqueous sodium hydroxide solution (0.81 mL), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: ethyl acetate/hexane 1/1—ethyl acetate) to give the title compound (35 mg).

Workup

  1. customThe reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: ethyl acetate/hexane 1/1—ethyl acetate)

Sources & evidence

ORD record
ord-c7aebbce7c7042b4b05f39b7ccdf28f6
Source dataset
uspto-grants-2007_05
Patent number
US07217697B2

Reaction notes

Loading…