Hydroxyamine hydrochloride → HCID 58043543, compound

HRID 1618055Notes

Reaction equation

HRID 1618055 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][C:4]([C:9](=O)[CH2:10][C@H:11]([C:19]2[CH:24]=[CH:23][C:22]([CH:25]3[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]3)=[CH:21][CH:20]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])=[CH:3]1.C(=O)([O-])O.[Na+].Cl.[NH2:45][OH:46]>C(O)C.O>[OH:46]/[N:45]=[C:9](/[C:4]1[CH:5]=[CH:6][C:7](=[O:8])[N:2]([CH3:1])[CH:3]=1)\[CH2:10][C@H:11]([C:19]1[CH:24]=[CH:23][C:22]([CH:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:32])[CH2:27][CH2:26]2)=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate2×HCID 66668277HCID 66668277, compound

Product 1

HCID 58043543HCID 58043543, compoundYield 102.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a microwave vial was added (R)-tert-butyl 4-(4-(3-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-3-oxo-1-o-tolylpropyl)phenyl)piperidine-1-carboxylate (35 mg, 68.0 μmol), sodium hydrogencarbonate (17.1 mg, 204 μmol) and hydroxylamine hydrochloride (14.2 mg, 204 μmol) in ethanol (1 mL) and water (0.02 mL). The vial was capped and heated at 120° C. for 15 min. The reaction mixture was poured onto aq. sat. sodium hydrogen carbonate solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated to afford the title compound (37 mg), which contained ca. 15% of the (Z)-stereoisomer. White foam; MS (ESI+): m/z=: 530.3 [M+H]+).

Workup

  1. customThe vial was capped
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-78aa1bb906094c579639a84ea05d5952
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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