Benzyl Bromide → 1-[4'-(4-Benzyloxymethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid

HRID 1528769Notes

Reaction equation

C([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH2:27][OH:28])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])C.[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[H-].[Na+]>O1CCOCC1>[CH2:29]([O:28][CH2:27][C:22]1[C:23]([CH3:26])=[N:24][O:25][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH:13]=[CH:14][C:9]([C:6]3([C:4]([OH:3])=[O:5])[CH2:7][CH2:8]3)=[CH:10][CH:11]=2)=[CH:16][CH:17]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1-[4′-(4-Hydroxymethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (0.100 g, 0.265 mmol) and benzyl bromide (0.031 mL, 0.265 mmol) were dissolved in dioxane. Sodium hydride (60% in mineral oil, 0.016 g, 0.398 mmol) was added and the reaction was heated to 60° C. overnight. Upon cooling the reaction was partitioned between EtOAc and H2O, acidified with 1 N HCl (aq.) and extracted with EtOAc. After drying the residue was purified by silica gel chromatography (EtOAc/hexanes) to afford the title compound.

Workup

temperatureUpon cooling the reaction
customwas partitioned between EtOAc and H2O
extractionextracted with EtOAc
customAfter drying the residue
customwas purified by silica gel chromatography (EtOAc/hexanes)

Sources & evidence

ORD record: ord-c2f1a6e704db4734a4ecf6dd4cf838ff
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090573B2

Reaction notes

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