Water → HCID 57709055, compound

HRID 546837Notes

Reaction equation

HRID 546837 reaction equation
[OH-:1].[K+].O.[CH2:4]([C:6]([C:25]1[CH:38]=[CH:37][C:28]([O:29][CH2:30][C@@H:31]2[O:35][C:34](=[O:36])[CH2:33][CH2:32]2)=[C:27]([CH3:39])[CH:26]=1)([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]([C:20]([OH:23])([CH3:22])[CH3:21])=[CH:18][CH:19]=2)=[C:11]([CH3:24])[CH:10]=1)[CH2:7][CH3:8])[CH3:5]>CO>[CH2:4]([C:6]([C:25]1[CH:38]=[CH:37][C:28]([O:29][CH2:30][C@H:31]([OH:35])[CH2:32][CH2:33][C:34]([OH:36])=[O:1])=[C:27]([CH3:39])[CH:26]=1)([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]([C:20]([OH:23])([CH3:22])[CH3:21])=[CH:18][CH:19]=2)=[C:11]([CH3:24])[CH:10]=1)[CH2:7][CH3:8])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 57709002HCID 57709002, compound

Product 1

HCID 57709055HCID 57709055, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1 N potassium hydroxide aqueous solution (0.1 mL, 0.1 mmol) and water (0.1 mL) were added to a solution of 5(R)-[4-(1-ethyl-1-{4-[5-(1-hydroxy-1-methyl-ethyl)-furan-2-yl]-3-methyl-phenyl}-propyl)-2-methyl-phenoxymethyl]-dihydro-furan-2-one (Example 19-(3); 2.8 mg, 0.006 mmol) in methanol (1 mL) at room temperature, and the mixture was stirred at the same temperature for one hour. The reaction solution was directly purified by silica gel chromatography (dichloromethane/methanol=8/3, saturated with water) to give the title compound (0.9 mg, 31%).

Workup

  1. customThe reaction solution was directly purified by silica gel chromatography (dichloromethane/methanol=8/3, saturated with water)

Sources & evidence

ORD record
ord-f02b6d379bce4865b1746a1a7937c36f
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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