Potassium Carbonate → HCID 86759680, compound

HRID 1816604Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:24][CH:25]([O:31][CH:32]([CH3:34])C)[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:13]=[CH:14][C:15]=1[O:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:35][C:36]1[CH:41]=[CH:40][C:39](OB(O)O)=[CH:38][CH:37]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:24][C:25]([O:31][CH2:32][CH2:34][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)([C:39]2[CH:40]=[CH:41][C:36]([F:35])=[CH:37][CH:38]=2)[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:13]=[CH:14][C:15]=1[O:16][S:17]([C:20]([F:22])([F:23])[F:21])(=[O:18])=[O:19])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 100 °C

Procedure

329 mg of ethyl 3-(3-[(tertiary butoxycarbonyl)amino]methyl-4-[(trifluoromethyl)sulfonyl]oxyphenyl)-2-isopropoxypropionate was dissolved in 4 ml toluene. 110 mg of 4-fluorophenylboric acid, 74 mg of tetrakistriphenyl phosphine palladium and 440 mg of potassium carbonate were added, followed by stirring overnight at 100° C. in a nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate, filtered through Celite and the filtrate was evaporated. The residue was purified by silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (6:1), 262 mg of ethyl 3-(3-[(tertiary butoxycarbonyl)amino]methyl-4-[(trifluoromethyl)sulfonyl]oxyphenyl)-2-(4-fluorophenyl)phenylpropoxypropionate was obtained.

Workup

filtrationfiltered through Celite
customthe filtrate was evaporated
customThe residue was purified by silica gel column chromatography
washfrom fractions eluted with hexane-ethyl acetate (6:1)

Sources & evidence

ORD record: ord-9f44710cb72749a597747718727763ab
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06884821B1

Reaction notes

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