Hydroxylamine → HCID 86683832, compound

HRID 572555Notes

Reaction equation

HRID 572555 reaction equation
[C:1]([C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]([CH3:20])[CH:9]([CH:17]([CH3:19])[CH3:18])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[C:5]([F:23])[CH:4]=1)#[N:2].[NH2:24][OH:25]>C(O)C.O>[NH2:2][C:1](=[N:24][OH:25])[C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]([CH3:20])[C@H:9]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH:17]([CH3:19])[CH3:18])=[C:5]([F:23])[CH:4]=1

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 66652839HCID 66652839, compound

Product 1

HCID 86683832HCID 86683832, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
-20 °C

Procedure

To a stirred solution of tert-butyl 2-[(4-cyano-2-fluorobenzyl)(methyl)amino]-3-methylbutanoate (3.4 g, 0.011 mol), in ethanol (30 mL), was added 50% aqueous. hydroxylamine (1.4 mL, 0.021 mol). The mixture was stirred at −20° C., for 12 h. The reaction mixture was diluted with water and extracted in dichloromethane (100 mL), dried over Na2SO4 and concentrated under reduce pressure. The solid was recrystallised with ethyl acetate (5 mL), filtered and dried under vacuum, affording the title compound as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 9.73 (s, 1H), 7.49 (m, 1H), 7.38 (m, 2H), 5.85 (s, 2H), 3.71 (d, J=14.2 Hz, 1H), 3.57 (d, J=14.2 Hz, 1H), 2.66 (d, J=10.7 Hz, 1H), 2.18 (s, 3H), 1.99-1.93 (m, 1H), 1.45 (s, 9H), 0.91-0.81 (m, 6H). LC/MS (Method B) 354.3 (M+H)+. HPLC (Method A) Rt: 2.66 min (Purity 98.6%).

Workup

  1. extractionextracted in dichloromethane (100 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe solid was recrystallised with ethyl acetate (5 mL)
  5. filtrationfiltered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-25a125f914ea459cb0c497be10270c8c
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

Loading…