Hydroxyamine hydrochloride → tert-butyl 1-(2-hydroxy-2-(4-(N'-hydroxycarbamimidoyl)phenyl)ethyl)azetidine-3-carboxylate

HRID 1948506Notes

Reaction equation

HRID 1948506 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([OH:22])[CH2:10][N:11]2[CH2:14][CH:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12]2)=[CH:5][CH:4]=1)#[N:2].C(=O)(O)[O-].[Na+].Cl.[NH2:29][OH:30]>CC(O)C.C(OCC)(=O)C>[OH:22][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([C:1](=[N:29][OH:30])[NH2:2])=[CH:8][CH:7]=1)[CH2:10][N:11]1[CH2:12][CH:13]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:14]1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 66955243Tert-butyl 1-(2-(4-cyanophenyl)-2-hydroxyethyl)azetidine-3-carboxylate

Product 1

HCID 76738020tert-butyl 1-(2-hydroxy-2-(4-(N'-hydroxycarbamimidoyl)phenyl)ethyl)azetidine-3-carboxylateYield 99.1%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of tert-butyl 1-(2-(4-cyanophenyl)-2-hydroxyethyl)azetidine-3-carboxylate (100 mg, 0.331 mmol) and sodium bicarbonate (111 mg, 1.323 mmol) in 2-propanol was added hydroxylamine hydrochloride (22.98 mg, 0.331 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 110 mg of tert-butyl 1-(2-hydroxy-2-(4-(N′-hydroxycarbamimidoyl)phenyl)ethyl)azetidine-3-carboxylate. MS (m+1)=336. HPLC Peak RT=0.91 minutes (Analytical Method B).

Workup

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

Sources & evidence

ORD record
ord-2e99549742444cc8bb830df608be4492
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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