Methanol → HCID 58237520, compound

HRID 885275Notes

Reaction equation

HRID 885275 reaction equation
C([O:8][C:9](=[O:22])[NH:10][C@@H:11]([CH3:21])[CH:12]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)O)C1C=CC=CC=1.CO.[OH-].[K+]>C1COCC1.CCOC(C)=O.[Cl-].[Na+].O>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C@H:12]2[O:22][C:9](=[O:8])[NH:10][C@H:11]2[CH3:21])=[CH:19][CH:18]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 67105651HCID 67105651, compound

Product 1

HCID 58237520HCID 58237520, compoundYield 17.5%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To [(S)-2-(4-Chloro-phenyl)-2-hydroxy-1-methyl-ethyl]-carbamic acid benzyl ester (2.7 mmol) in THF:MeOH was added 7.5N aqueous potassium hydroxide (10 mL), and the reaction was stirred at room temperature for 3 hours. Once no starting material was seen by analytical LCMS, the mixture was diluted with EtOAc and brine, and the organic layer was separated and purified by silica gel chromatography to give the desired product (0.1 g).

Workup

  1. customthe organic layer was separated
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-821c53f4aad54219b0e0bc56d3c2870a
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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