Hydroxyamine hydrochloride → HCID 87214058, compound

HRID 1948492Notes

Reaction equation

HRID 1948492 reaction equation
[OH:1][C@@H:2]([C:16]1[CH:21]=[CH:20][C:19](/[C:22](=[N:24]/[OH:25])/[NH2:23])=[CH:18][CH:17]=1)[CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][C@H:6]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:5]1.C(=O)(O)[O-].[Na+].Cl.NO>CC(O)C.C(OCC)(=O)C>[OH:1][CH:2]([C:16]1[CH:17]=[CH:18][C:19](/[C:22](=[N:24]/[OH:25])/[NH2:23])=[CH:20][CH:21]=1)[CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][C@H:6]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:5]1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 58374196ethyl 2-[(3R)-1-[(2S)-2-hydroxy-2-[4-[(Z)-N'-hydroxycarbamimidoyl]phenyl]ethyl]piperidin-3-yl]acetate

Product 1

HCID 87214058HCID 87214058, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of ethyl 2-((R)-1-((S)-2-hydroxy-2-(4-((Z)—N′-hydroxycarbamimidoyl)phenyl)ethyl)piperidin-3-yl)acetate (18C-Isomer A) and sodium bicarbonate (378 mg, 4.50 mmol) in 2-propanol (10 mL) was added hydroxylamine hydrochloride (156 mg, 2.250 mmol). The reaction mixture was heated at 85° C. overnight. The reaction mixture was diluted with ethyl acetate and washed with H2O. The organic layer was dried with MgSO4, filtered, and concentrated to yield 346 mg of ethyl 2-((3R)-1-(2-hydroxy-2-(4-((Z)—N′-hydroxycarbamimidoyl)phenyl)ethyl)piperidin-3-yl)acetate. MS (M+1)=336. HPLC Peak RT=0.12 minutes.

Workup

  1. washwashed with H2O
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7ae443f4a2074e91bedb09754ac8230f
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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