Trifluoromethanesulfonic acid → HCID 118117188, compound

HRID 1747215Notes

Reaction equation

HRID 1747215 reaction equation
C1C(=O)N([I:8])C(=O)C1.[CH3:9][O:10][C:11]1[CH:24]=[CH:23][C:14]([CH2:15][C@H:16]2[NH:21][C:20](=[O:22])[CH2:19][O:18][CH2:17]2)=[CH:13][CH:12]=1.FC(F)(F)S(O)(=O)=O>C(Cl)Cl>[I:8][C:24]1[CH:23]=[C:14]([CH:13]=[CH:12][C:11]=1[O:10][CH3:9])[CH2:15][C@H:16]1[NH:21][C:20](=[O:22])[CH2:19][O:18][CH2:17]1

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 120273N-IodosuccinimideHCID 118117674HCID 118117674, compound

Product 1

HCID 118117188HCID 118117188, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of NIS (559 mg, 2.49 mmol) in DCM (3 mL) was added dropwise to a RT solution of (R)-5-(4-methoxy-benzyl)-morpholin-3-one C-6 (500 mg, 2.26 mmol) and trifluoromethanesulfonic acid (220 μL, 2.49 mmol) in DCM (3 mL) under argon and the resulting mixture was stirred for 40 min. The reaction was quenched with sat. aq. NaHCO3 and the layers were separated. The organic layer was washed with water (2×), dried over Na2SO4, filtered and evaporated in vacuo to give the crude product that was purified by flash chromatography (eluting with a gradient of 50% to 100% EtOAc in hexane) to give the title compound as a pale yellow solid. LC-MS B: tR=0.62 min; [M+H+MeCN]+=388.95.

Workup

  1. customThe reaction was quenched with sat. aq. NaHCO3
  2. customthe layers were separated
  3. washThe organic layer was washed with water (2×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give the crude product that
  8. customwas purified by flash chromatography (
  9. washeluting with a gradient of 50% to 100% EtOAc in hexane)

Sources & evidence

ORD record
ord-856dc819d97a401cb3082627e249f729
Source dataset
uspto-grants-2015_10
Patent number
US09150566B2

Reaction notes

Loading…