Hydroxyamine hydrochloride → HCID 145785766, compound

HRID 456767Notes

Reaction equation

HRID 456767 reaction equation
[C:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([C@@H:10]1[C@H:15]2[CH2:16][C@H:12]([C@H:13]([O:17][CH2:18][CH:19]=O)[CH2:14]2)[N:11]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:9])#[N:2].Cl.[NH2:29][OH:30].C([O-])(=O)C.[Na+]>C(O)C.O.[Cl-].[Na+].O>[C:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([C@@H:10]1[C@H:15]2[CH2:16][C@H:12]([C@H:13]([O:17][CH2:18]/[CH:19]=[N:29]/[OH:30])[CH2:14]2)[N:11]1[C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])=[O:9])#[N:2]

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86598909HCID 86598909, compound

Product 1

HCID 145785766HCID 145785766, compoundYield 77.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of tert-butyl (1R,3S,4S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-(2-oxoethoxy)-2-azabicyclo[2.2.1]heptane-2-carboxylate obtained in Example 25-1 (163 mg) in ethanol (6 mL) and water (1 mL), were added hydroxylamine hydrochloride (36 mg) and sodium acetate (46 mg). The mixture was stirred at reflux for 20 minutes. To the resulting mixture, brine was added. The mixture extracted with ethyl acetate. The combined organic phase was washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate to give the target compound (131 mg).

Workup

  1. temperatureat reflux for 20 minutes
  2. extractionThe mixture extracted with ethyl acetate
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-296392ba0206409894205b3b215ceae1
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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