2,6-Di-tert-butyl-4-methylpyridine → HCID 118260144, compound

HRID 1779205Notes

Reaction equation

HRID 1779205 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:34]=[CH:35]/[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42](=[O:50])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[C@@:22]([OH:33])([CH2:30][CH2:31][OH:32])[C:23]([O:25][C:26](C)(C)C)=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C.F[B-](F)(F)F.C[O+](C)C>ClCCl>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:34]=[CH:35]/[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42](=[O:50])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[C@@:22]([OH:33])([CH2:30][CH2:31][OH:32])[C:23]([O:25][CH3:26])=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:11]=1)[C:2]#[C:3][CH3:4]

Participants

5

Reactant 3

HCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 90060183HCID 90060183, compound

Product 1

HCID 118260144HCID 118260144, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of No. 5217614, tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-(2-hydroxy-ethyl)-12-oxo-nonadec-4-enoate (25 mg, 0.0357 mmol), 2,6-di-tert-butyl-4-methyl pyridine (15.4 mg, 0.075 mmol), and dichloromethane (2 mL) was added trimethyloxonium tetrafluoroborate (11 mg, 0.075 mmol) and the mixture was stirred at room temperature for 21 hours. After confirming the consumption of the starting materials by LCMS, methanol and water were added. The organic solvent was distilled off under reduced pressure. The resulting residue was purified by preparative HPLC and then freeze-dried to obtain the title compound (7 mg, 30% yield, white solid).

Workup

  1. additionTo a mixture of No
  2. customthe consumption of the starting materials by LCMS, methanol and water
  3. additionwere added
  4. distillationThe organic solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by preparative HPLC
  6. customfreeze-dried

Sources & evidence

ORD record
ord-0399c31b90134fb68f5a7335115ba1d1
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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