Sodium Hydroxide → HCID 66886215, compound

HRID 2353020Notes

Reaction equation

HRID 2353020 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH:22]([O:25][CH3:26])[O:23][CH3:24])=[CH:15][CH:14]=1)[CH:8]=[CH:7]2.[C:27]([O:33][C@@H:34]1[C@@H:39]([O:40][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[C@H:38]([O:47][C:48](=[O:53])[C:49]([CH3:52])([CH3:51])[CH3:50])[C@@H:37]([CH2:54][O:55][C:56](=[O:61])[C:57]([CH3:60])([CH3:59])[CH3:58])[O:36][C@@H:35]1Br)(=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29].[OH-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.C(Cl)Cl>[CH3:24][O:23][CH:22]([O:25][CH3:26])[CH2:21][CH2:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][N:9]2[C:10]3[C:6](=[CH:5][CH:4]=[CH:3][C:2]=3[O:1][C@@H:35]3[O:36][C@H:37]([CH2:54][O:55][C:56](=[O:61])[C:57]([CH3:60])([CH3:59])[CH3:58])[C@@H:38]([O:47][C:48](=[O:53])[C:49]([CH3:50])([CH3:51])[CH3:52])[C@H:39]([O:40][C:41](=[O:46])[C:42]([CH3:43])([CH3:44])[CH3:45])[C@H:34]3[O:33][C:27](=[O:32])[C:28]([CH3:31])([CH3:29])[CH3:30])[CH:7]=[CH:8]2)=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 10886360((2R,3R,4S,5R,6R)-6-bromo-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl)methyl 2,2-dimethylpropanoateHCID 57584214HCID 57584214, compound

Product 1

HCID 66886215HCID 66886215, compoundYield 27.8%

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 7-hydroxy-1-{2-[4-(3,3-dimethoxy-propoxy)phenyl]ethyl}-1H-indole (1.57 g), 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide (2.56 g) and benzyltri-(n-butyl)ammonium chloride (1.38 g) in methylene chloride (15 mL) was added 5 mol/L aqueous sodium hydroxide solution (2.7 mL), and the mixture was stirred at room temperature for 2 days. The reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent: n-hexane/ethyl acetate=1/1), and purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=6/1-4/1) to give 1-{2-[4-(3,3-dimethoxypropoxy)phenyl]ethyl}-7-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-indole (1.05 g). This material was dissolved in acetone (12 mL). To the solution were added water (6 mL) and oxalic acid dihydrate, and the mixture was heated for reflux for 2 hours. To the reaction mixture was added piperazine (0.64 g), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The ethyl acetate solution was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=4/1), and purified by column chromatography on aminopropylated silica gel (n-hexane/ethyl acetate=4/1-3/1-2/1) to give the title compound (0.31 g).

Workup

  1. customThe reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent: n-hexane/ethyl acetate=1/1)
  2. custompurified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=6/1-4/1)

Sources & evidence

ORD record
ord-ac75b8f4401b4d1ead930bd6dedf4207
Source dataset
uspto-grants-2010_07
Patent number
US07749972B2

Reaction notes

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