Nitric Acid → (S)-4-[(S)-2-(4-nitro-phenyl)-butyl]-4,5-dihydro-oxazol-2-ylamine

HRID 1805219Notes

Reaction equation

[N+:1]([O-:4])(O)=[O:2].[C:5]1([C@@H:11]([CH2:19][CH3:20])[CH2:12][C@H:13]2[CH2:17][O:16][C:15]([NH2:18])=[N:14]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+]>C(OCC)(=O)C.C1COCC1>[N+:1]([C:8]1[CH:7]=[CH:6][C:5]([C@@H:11]([CH2:19][CH3:20])[CH2:12][C@H:13]2[CH2:17][O:16][C:15]([NH2:18])=[N:14]2)=[CH:10][CH:9]=1)([O-:4])=[O:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To stirred nitric acid (9.5 ml, 65% conc.) at room temperature was added (S)-4-((S)-2-phenyl-butyl)-4,5-dihydro-oxazol-2-ylamine (1.5 g, CAS 1043495-96-0) and the mixture was then heated at 60° C. for 3 hours. The mixture was then cooled in an ice-bath before being made basic by careful addition of 30% aq. sodium hydroxide solution. The resulting mixture was diluted with ethyl acetate/THF (1:1) and the phases were separated. The organic phase was washed with saturated brine, dried over sodium sulphate and concentrated in vacuo to give (S)-4-[(S)-2-(4-nitro-phenyl)-butyl]-4,5-dihydro-oxazol-2-ylamine (1.89 g, quant.) as a yellow solid. MS (ISP): 264.2 ([M+H]+).

Workup

temperatureThe mixture was then cooled in an ice-bath
customthe phases were separated
washThe organic phase was washed with saturated brine
dry with materialdried over sodium sulphate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a1964a2619cf4d728adc8777906bc354
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354441B2

Reaction notes

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