Trifluoroacetic acid → HCID 68900372, compound

HRID 900318Notes

Reaction equation

HRID 900318 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([S:13][CH3:14])=[N:6][CH:7]=[N:8]2.C(O)(C(F)(F)F)=O.[CH2:22]([O:25][C:26]([C@@H:28]1[CH2:33][CH2:32][NH:31][CH2:30][C@@H:29]1[C:34]([O:36][CH3:37])=[O:35])=[O:27])[CH:23]=[CH2:24]>ClC(Cl)C>[CH2:22]([O:25][C:26]([C@@H:28]1[CH2:33][CH2:32][N:31]([CH2:2][C:3]2[CH:12]=[CH:11][CH:10]=[C:9]3[C:4]=2[C:5]([S:13][CH3:14])=[N:6][CH:7]=[N:8]3)[CH2:30][C@@H:29]1[C:34]([O:36][CH3:37])=[O:35])=[O:27])[CH:23]=[CH2:24]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 58711717HCID 58711717, compoundHCID 66953049HCID 66953049, compound

Product 1

HCID 68900372HCID 68900372, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 15A (2.02 g, 7.5 mmol), TFA salt of (3R,4R)-methyl 4-(allyloxycarbonyl)piperidine-3-carboxylate (2.8 g, 7.87 mmol), (prepared as described in U.S. patent application Ser. No. 11/019,901) and TEA (3.14 ml, 22.5 mmol) in dichloroethane (50 ml) was heated at 70° C. for 1 h. After cooling to room temperature, the reaction mixture was washed with water, dried and concentrated in vacuo. Purification using silica gel flash column (DCM/MeOH=98/2) gave 15B (2.91 g, 90%) as a solid. The compound has an analytical HPLC retention time=1.547 min (Chromolith SpeedROD column 4.6×50 mm, 10-90% aqueous methanol containing 0.1% TFA over 4 minutes, 4 mL/min, monitoring at 254 nm) and a LC/MS M++H=431+.

Workup

  1. custom(prepared
  2. washthe reaction mixture was washed with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customPurification

Sources & evidence

ORD record
ord-8ba377c6ff214a7d93ba4f3e1933c547
Source dataset
uspto-grants-2008_04
Patent number
US07358256B2

Reaction notes

Loading…