HCID 117988560, compound → (2S,5R)-N-(2-Benzyloxycarbonylaminoethoxy)-5-(benzyloxyamino)piperidine-2-carboxamide

HRID 711007Notes

Reaction equation

HRID 711007 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][O:14][NH:15][C:16]([C@@H:18]1[CH2:23][CH2:22][C@@H:21]([NH:24][O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:20][N:19]1C(OC(C)(C)C)=O)=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCOCC1>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][O:14][NH:15][C:16]([C@@H:18]1[CH2:23][CH2:22][C@@H:21]([NH:24][O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:20][NH:19]1)=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 117988560HCID 117988560, compound

Product 1

HCID 117988576(2S,5R)-N-(2-Benzyloxycarbonylaminoethoxy)-5-(benzyloxyamino)piperidine-2-carboxamideYield 95.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(2S,5R)—N-(2-Benzyloxycarbonylaminoethoxy)-5-(benzyloxyamino)-1-(tert-butoxycarbonyl)piperidine-2-carboxamide (2.91 g, 5.362 mmol) was dissolved in 1,4-dioxane (5 mL), to which was added under ice cooling 4M hydrochloric acid-dioxane solution (10 mL). After stirring for 2 h., the mixture was concentrated under reduced pressure, dissolved in water (30 mL), and washed with ether. The aqueous layer was ice-cooled, and pH was set to ca. pH 7 with 5M sodium hydroxide and acetic acid, and then extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and then the solvent was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (chloroform chloroform/methanol=3:1) to afford 2.27 g of the title compound (yield 95%).

Workup

  1. additionwas added under ice cooling 4M hydrochloric acid-dioxane solution (10 mL)
  2. concentrationthe mixture was concentrated under reduced pressure
  3. dissolutiondissolved in water (30 mL)
  4. washwashed with ether
  5. temperaturecooled
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationthe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-162f213b949745d8b53d361cf4ca5bb1
Source dataset
uspto-grants-2015_11
Patent number
US09181250B2

Reaction notes

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