Ethanol → EtOAc EtOH H2O NH4OH

HRID 1602629Notes

Reaction equation

HRID 1602629 reaction equation
[C:1]([NH:4][C@@H:5]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]=1[CH2:19][CH3:20])[CH2:6][C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].[OH-:21].[Na+].[CH2:23]([OH:25])[CH3:24]>>[CH3:23][CH2:24][O:9][C:7]([CH3:6])=[O:8].[CH3:2][CH2:1][OH:3].[NH4+:4].[OH-:25].[OH2:21].[C:1]([NH:4][C@@H:5]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]=1[CH2:19][CH3:20])[CH2:6][C:7]([OH:9])=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 86754784HCID 86754784, compound

Product 2

HCID 86752451EtOAc EtOH H2O NH4OHHCID 86754784HCID 86754784, compound

Procedure

A mixture of 7-2 (60 mg, 0.11 mmol), 1N NaOH (132 μL), and ethanol (1 mL) was stirred at ambient temperature for 1 hr, followed by concentration. Flash chromatography (silica, 25:10:1:1 to 15:10:1:1 EtOAc/EtOH/NH4OH/H2O) gave 7-3 as a white solid.

Workup

  1. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-6951a14ada524877baa328cdc848907f
Source dataset
uspto-grants-1999_11
Patent number
US05981546

Reaction notes

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