Sodium Hydroxide → HCID 68537658, compound

HRID 2223600Notes

Reaction equation

HRID 2223600 reaction equation
[CH2:1]([O:8][C:9]([C:11]([CH3:31])([CH3:30])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]2[C:22](=[O:29])[NH:23][NH:24][C:25]=2[CH:26]([CH3:28])[CH3:27])=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32][C:33]([O:35][CH2:36][C@H:37]1[O:42][C@H:41](Br)[C@H:40]([O:44][C:45]([CH3:47])=[O:46])[C@@H:39]([O:48][C:49]([CH3:51])=[O:50])[C@@H:38]1[O:52][C:53]([CH3:55])=[O:54])=[O:34].[OH-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.ClCCl>[C:45]([O:44][C@@H:40]1[C@@H:39]([O:48][C:49](=[O:50])[CH3:51])[C@H:38]([O:52][C:53](=[O:54])[CH3:55])[C@@H:37]([CH2:36][O:35][C:33](=[O:34])[CH3:32])[O:42][C@H:41]1[O:29][C:22]1[C:21]([CH2:20][C:17]2[CH:16]=[CH:15][C:14]([O:13][CH2:12][C:11]([C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])([CH3:31])[CH3:30])=[CH:19][CH:18]=2)=[C:25]([CH:26]([CH3:27])[CH3:28])[NH:24][N:23]=1)(=[O:46])[CH3:47]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 101776alpha-D-Glucopyranosyl bromide, tetraacetateHCID 68535856HCID 68535856, compound

Product 1

HCID 68537658HCID 68537658, compoundYield 62.9%

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{[4-(2-benzyloxycarbonyl-2-methylpropoxy)phenyl]methyl}-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one (0.25 g), acetobromo-α-D-glucose (0.48 g) and benzyltri(n-butyl)ammonium chloride (0.18 g) in dichloromethane (5 mL) was added 5 mol/L aqueous sodium hydroxide solution (0.35 mL), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent: n-hexane/ethyl acetate=1/1-1/3) to give the title compound (0.28 g).

Workup

  1. customThe reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent: n-hexane/ethyl acetate=1/1-1/3)

Sources & evidence

ORD record
ord-edf9e96f08ea4e678cf400091775201e
Source dataset
uspto-grants-2008_05
Patent number
US07375087B2

Reaction notes

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