2,6-Di-tert-butyl-4-methylpyridine → HCID 90060265, compound
Reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:19][C:20]([C@@H:22](/[CH:35]=[CH:36]/[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43](=[O:51])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[C@@:23]([OH:34])([CH2:31][CH2:32][OH:33])[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:21])[C:14](=[O:18])[N:15]([CH3:17])[CH3:16])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].F[B-](F)(F)F.[CH3:57][O+](C)C.C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C>ClCCl>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C@H:13]([NH:19][C:20]([C@@H:22](/[CH:35]=[CH:36]/[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43](=[O:51])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[C@@:23]([OH:34])([CH2:31][CH2:32][O:33][CH3:57])[C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])=[O:21])[C:14](=[O:18])[N:15]([CH3:17])[CH3:16])=[CH:10][CH:11]=1)[C:2]#[C:3][CH3:4]Participants
5
Procedure
tert-Butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-dimethylcarbamoyl-ethylcarbamoyl]-2-hydroxy-2-(2-hydroxy-ethyl)-12-oxo-nonadec-4-enoate (15.0 mg, 21.5 μmol) was dissolved in dichloromethane (0.5 mL), and trimethyloxonium tetrafluoroborate (6.7 mg, 45.1 μmol) and 2,6-di-tert-butyl-4-methylpyridine (9.3 mg, 45.1 μmol) were added at 0° C. The mixture was stirred at room temperature for 5 hours. The reaction mixture was purified by preparative HPLC to obtain the title compound (3.5 mg, 22% yield).
Workup
- customThe reaction mixture was purified by preparative HPLC
Sources & evidence
- ORD record
- ord-8ad16aff610a49519fa9579e19fa97ca
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266853B2
Reaction notes
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