Water → HCID 178519416, compound

HRID 1160263Notes

Reaction equation

CCCC[N+](CCCC)(CCCC)CCCC.[F-:18].O.[Cl:20][C:21]1[CH:22]=[C:23]([C:46]2[CH:51]=[CH:50][C:49]([C:52]([N:54]3[CH2:59][CH2:58][CH:57]([C:60]([F:63])([F:62])[F:61])[CH2:56][CH2:55]3)=[O:53])=[CH:48][CH:47]=2)[CH:24]=[C:25]([Cl:45])[C:26]=1[CH2:27][C@@H:28]1[CH2:32][CH2:31][N:30]([C@H:33]2[CH2:38][CH2:37][C@H:36](OS(C)(=O)=O)[CH2:35][CH2:34]2)[C:29]1=[O:44]>C(#N)C>[Cl:20][C:21]1[CH:22]=[C:23]([C:46]2[CH:51]=[CH:50][C:49]([C:52]([N:54]3[CH2:55][CH2:56][CH:57]([C:60]([F:62])([F:61])[F:63])[CH2:58][CH2:59]3)=[O:53])=[CH:48][CH:47]=2)[CH:24]=[C:25]([Cl:45])[C:26]=1[CH2:27][C@@H:28]1[CH2:32][CH2:31][N:30]([C@H:33]2[CH2:38][CH2:37][C@@H:36]([F:18])[CH2:35][CH2:34]2)[C:29]1=[O:44]

Participants

Conditions

Temperature: 80 °C

Procedure

Dissolve TBAF.3H2O (0.436 g, 1.36 mmol) in 5 ml of acetonitrile. Add water (0.05 ml. 2.72 mmol) and stir for 10 minutes. Add Methanesulfonic acid trans-4-{(R)-3-[3,5-dichloro-4′-(4-trifluoromethyl-piperidine-1-carbonyl)-biphenyl-4-ylmethyl]-2-oxo-pyrrolidin-1-yl}-cyclohexyl ester (Preparation 24) (0.458 g, 0.68 mmol). Stir at 80° C. for 12 hours. Quench with saturated NaHCO3 and extract with ethyl acetate. Wash the extract with brine. Dry over magnesium sulfate, filter, and concentrate. After flash column chromatography receive 0.036 g (9%) of the title compound: Mass spectrum (apci) m/z=599 (M+H).

Workup

customQuench with saturated NaHCO3
extractionextract with ethyl acetate
washWash the
extractionextract with brine
dry with materialDry over magnesium sulfate
filtrationfilter
concentrationconcentrate

Sources & evidence

ORD record: ord-17f0e6d199d4448eb87a392f6c085445
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816349B2

Reaction notes

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