Water → HCID 11517239, compound

HRID 2353021Notes

Reaction equation

HRID 2353021 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[O:19][C@@H:20]3[O:46][C@H:45]([CH2:47][O:48]C(=O)C(C)(C)C)[C@@H:37]([O:38]C(=O)C(C)(C)C)[C@H:29]([O:30]C(=O)C(C)(C)C)[C@H:21]3[O:22]C(=O)C(C)(C)C)[CH:12]=[CH:11]2)=[CH:4][CH:3]=1.O.O.[OH-].[Li+]>CO>[C@@H:20]1([O:19][C:17]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:18]=2[N:10]([CH2:9][CH2:8][C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=2)[CH:11]=[CH:12]3)[O:46][C@H:45]([CH2:47][OH:48])[C@@H:37]([OH:38])[C@H:29]([OH:30])[C@H:21]1[OH:22]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 57584217HCID 57584217, compound

Product 1

HCID 11517239HCID 11517239, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[2-(4-hydroxyphenyl)ethyl]-7-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-indole (50 mg) in methanol (1 mL) were added water (0.1 mL) and lithium hydroxide monohydrate (11 mg), and the mixture was stirred at room temperature overnight. The reaction mixture was purified by column chromatography on silica gel (eluent: methylene chloride/methanol=8/1-5/1) to give the title compound (20 mg).

Workup

  1. customThe reaction mixture was purified by column chromatography on silica gel (eluent: methylene chloride/methanol=8/1-5/1)

Sources & evidence

ORD record
ord-1d68655f3a4e456dae808dd5a2d11a68
Source dataset
uspto-grants-2010_07
Patent number
US07749972B2

Reaction notes

Loading…