N,N,N-Tributylbutan-1-aminium fluoride--hydrogen fluoride (1/1/2) → HCID 178472376, compound

HRID 928145Notes

Reaction equation

HRID 928145 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2([C@H:10]3[CH2:15][CH2:14][C@H:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]3)[CH2:9][O:8]2)=[N:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[FH:38].F.[F-]>O>[Br:1][C:2]1[S:6][C:5]([C:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]2)([OH:8])[CH2:9][F:38])=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 11748636N,N,N-Tributylbutan-1-aminium fluoride--hydrogen fluoride (1/1/2)HCID 178472329HCID 178472329, compound

Product 1

HCID 178472376HCID 178472376, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a vial were added ethyl trans-4-[2-(5-bromo-1,3-thiazol-2-yl)oxiran-2-yl]-cyclohexanecarboxylate (101 mg, 0.28 mmol) and tetra-N-butylammonium dihydrogentrifluoride (422 mg, 1.34 mmol). The mixture was heated at 120° C. for 3 h 45 min. The mixture was diluted with water, and extracted with EtOAc. The organic phase was washed with water, brine, dried over sodium sulfate and concentrated to afford racemic ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)-2-fluoro-1-hydroxyethyl]cyclohexane-carboxylate which was used without further purification. MS ESI calc'd. for C14H19BrFNO3S [M+H]+ 380, 382. found 380, 382.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-579d1b4e22c44a6ca0138c2ff0bc5bc0
Source dataset
uspto-grants-2016_03
Patent number
US09290490B2

Reaction notes

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