Pyridine → HCID 58109145, compound
Reaction equation
[C:1]([NH:4][NH:5][C:6](=O)[CH2:7][C@@:8]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=2)[CH3:16])[CH2:10][CH2:9]1)(=[O:3])[CH3:2].N1C=CC=CC=1.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O>C(Cl)Cl>[Br:23][C:20]1[CH:19]=[CH:18][C:17]([C@@H:15]([N:11]2[CH2:10][CH2:9][C@:8]([CH2:7][C:6]3[O:3][C:1]([CH3:2])=[N:4][N:5]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:13][C:12]2=[O:14])[CH3:16])=[CH:22][CH:21]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
To a solution of N′-acetyl-2-((S)-3-((S)-1-(4-bromophenyl)ethyl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)acetohydrazide (100 mg, 0.21 mmol) in CH2Cl2 (2 mL) was added pyridine (37 mg, 0.46 mmol). The reaction mixture was cooled to −10° C. and triflic anhydride (125 mg, 0.44 mmol) was added. The reaction mixture was stirred at −10° C. for 1 h and at 0° C. for 1 h. The mixture was warmed to rt and quenched by addition of satd aq NaHCO3. The aqueous layer was washed with CH2Cl2 and the combined organic phase was concentrated to give the crude product, which was purified by preparative TLC to afford (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-((5-methyl-1,3,4-oxadiazol-2-yl)methyl)-6-phenyl-1,3-oxazinan-2-one (56 mg, 58%). 1H NMR (400 MHz, CDCl3): δ=1.51 (d, 3H), 2.32-2.41 (m, 2H), 2.48 (s, 3H), 2.73 (m, 2H), 3.16 (m, 2H), 5.49 (m, 1H), 6.78 (d, 2H), 7.24 (m, 2H), 7.32 (m, 2H), 7.41 (m, 3H).
Workup
- temperatureThe mixture was warmed to rt
- customquenched by addition of satd aq NaHCO3
- washThe aqueous layer was washed with CH2Cl2
- concentrationthe combined organic phase was concentrated
- customto give the crude product, which
- customwas purified by preparative TLC
Sources & evidence
- ORD record
- ord-51a11fb6b52a4a5bb4280674b0439d2d
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575156B2
Reaction notes
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