Water → HCID 118037594, compound

HRID 2272494Notes

Reaction equation

HRID 2272494 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH2:16]([C:18]1[C:19](=[O:38])[N:20]([CH:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]2)[CH:21]=[CH:22][C:23]=1O)[CH3:17].O>N1C=CC=CC=1>[CH2:16]([C:18]1[C:19](=[O:38])[N:20]([CH:25]2[CH2:26][CH2:27][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:29][CH2:30]2)[CH:21]=[CH:22][C:23]=1[O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 67749Trifluoromethanesulfonic anhydrideHCID 118037429HCID 118037429, compound

Product 1

HCID 118037594HCID 118037594, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Trifluoromethanesulfonic anhydride (1.76 mL) was added at 0 C to a mixture of tert-butyl 4-(3-ethyl-4-hydroxy-2-oxopyridin-1(2H)-yl)piperidine-1-carboxylate (1.12 g) in pyridine (17.4 mL), and the mixture was stirred at 0 C for 30 minutes in a nitrogen atmosphere. Water was added thereto, and then, the solvent was distilled off under reduced pressure. Water was added again to the residue, followed by extraction with ethyl acetate. The obtained organic layer was washed with 1 M hydrochloric acid and saturated saline in this order and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (1.14 g).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionWater was added again to the residue
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe obtained organic layer was washed with 1 M hydrochloric acid and saturated saline in this order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-16df4ddc24ab4bdc96f6e9047e1399d2
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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