Ethyl Acetate → HCID 90203479, compound

HRID 927044Notes

Reaction equation

[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[C:9]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[N:10][O:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[C:27]1([CH2:33][CH2:34][CH2:35]Br)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(OCC)(=O)C>CN(C=O)C.CCCCCC>[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[C:9]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:35][CH2:34][CH2:33][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:17][CH:18]=2)=[N:10][O:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of [3-(4-hydroxy-phenyl)-isoxazol-4-yl]-carbamic acid tert-butyl ester (38 mg, 0.137 mmol) in DMF (1 mL) was added K2CO3 (20 mg, 0.145 mmol) and 3-phenyl-1-bromopropane (20 μL, 0.132 mmol). After stirring for 1 h at rt and 14 h at 50° C., the reaction mixture was cooled stirred for 6 h at rt. The reaction mixture was loaded directly onto silica gel. {3-[4-(3-Phenyl-propoxy)-phenyl]-isoxazol-4-yl}-carbamic acid tert-butyl ester was isolated as a white solid by column chromatography (10% ethyl acetate in hexane).

Workup

temperaturethe reaction mixture was cooled
stirringstirred for 6 h at rt

Sources & evidence

ORD record: ord-88b49b43b9ff42afb1f51a455977b87e
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290465B2

Reaction notes

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