Acetic Acid → (2S,5R)-N-(2-tert-Butoxycarbonylaminoethoxy)-5-(benzyloxyamino)piperidine-2-carboxamide

HRID 711004Notes

Reaction equation

HRID 711004 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][NH:12][C:13]([C@@H:15]1[CH2:20][CH2:19][C@@H:18]([NH:21][O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:17][N:16]1C(=O)C(F)(F)F)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Na+].C(O)(=O)C>O1CCOCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][NH:12][C:13]([C@@H:15]1[CH2:20][CH2:19][C@@H:18]([NH:21][O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:17][NH:16]1)=[O:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 117987976(2S,5R)-N-(2-tert-Butoxycarbonylaminoethoxy)-5-(benzyloxyamino)-1-(2,2,2-trifluoroacetyl)piperidine-2-carboxamide

Product 1

HCID 117988372(2S,5R)-N-(2-tert-Butoxycarbonylaminoethoxy)-5-(benzyloxyamino)piperidine-2-carboxamideYield 95.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(2S,5R)—N-(2-tert-butoxycarbonylaminoethoxy)-5-(benzyloxyamino)-1-(2,2,2-trifluoroacetyl)piperidine-2-carboxamide (1.07 g, 2.06 mmol) was dissolved in 1,4-dioxane (4.2 mL), to which was added water (1.1 mL), and followed by ice cooling. To this was added 1M sodium hydroxide aqueous solution (6.3 mL), and followed by reaction at the same temperature for 2.5 h. pH was adjusted to ca. pH 7 by the addition of acetic acid to the reaction mixture. The organic solvent was distilled off under reduced pressure. The resulting aqueous solution was extracted with ethyl acetate. After the organic layer was washed with saturated brine, and dehydrated with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting oil residue was purified by silica gel column chromatography (ethyl acetate/methanol=9/1) to afford 0.80 g of the title compound (yield 93%).

Workup

  1. customfollowed by reaction at the same temperature for 2.5 h.
  2. distillationThe organic solvent was distilled off under reduced pressure
  3. extractionThe resulting aqueous solution was extracted with ethyl acetate
  4. washAfter the organic layer was washed with saturated brine
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting oil residue was purified by silica gel column chromatography (ethyl acetate/methanol=9/1)

Sources & evidence

ORD record
ord-a19a1a1ce3834b39b8cde40177c798c7
Source dataset
uspto-grants-2015_11
Patent number
US09181250B2

Reaction notes

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