2,6-Lutidine → HCID 58530111, compound

HRID 451288Notes

Reaction equation

HRID 451288 reaction equation
O[C@@H:2]1[CH2:6][N:5]([C:7](=[O:12])[C:8]([F:11])([F:10])[F:9])[C@H:4]([C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])[CH2:3]1.N1C(C)=CC=CC=1C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH2:42]([O:49][NH2:50])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C(#N)C.C(OCC)(=O)C>[CH2:42]([O:49][NH:50][C@H:2]1[CH2:6][N:5]([C:7](=[O:12])[C:8]([F:11])([F:10])[F:9])[C@H:4]([C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])[CH2:3]1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

7

Reactant 4

HCID 79372,6-Lutidine2×HCID 67749Trifluoromethanesulfonic anhydrideHCID 102313O-BenzylhydroxylamineHCID 58530065HCID 58530065, compound

Product 1

HCID 58530111HCID 58530111, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of allyl (4S)-4-hydroxy-1-(trifluoroacetyl)-L-prolinate (844 mg, 3.16 mmol) in acetonitrile (16 mL) was cooled to −10° C. and 2,6-lutidine (0.62 mL, 5.32 mmol) was added followed by trifluoromethanesulfonic anhydride (0.85 mL, 5.15 mmol). After addition, the temperature was allowed to warm to 0° C. The reaction mixture was stirred at 0° C. for 1 hour then O-benzylhydroxylamine (1 mL, 8.67 mmol) was added followed by 2,6-lutidine (0.62 mL, 5.32 mmol). The reaction mixture was allowed to warm to room temperature overnight. The reaction mixture was then diluted with ethyl acetate and washed with 5% sodium bicarbonate solution and brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The tan oil residue (2.57 g) was chromatographed on silica gel eluted initially with 95:5 dichloromethane:ethyl acetate and finally with 80:20 dichloromethane:ethyl acetate to afford the title compound as a pale yellow solid.

Workup

  1. additionAfter addition
  2. temperatureto warm to room temperature overnight
  3. washwashed with 5% sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe tan oil residue (2.57 g) was chromatographed on silica gel
  8. washeluted initially with 95:5 dichloromethane

Sources & evidence

ORD record
ord-7bd11988d5474170a9c29f4c3c9f0545
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

Loading…