Acetonitrile--water (1/1) → (S)-6-(2-amino-2-methylpropyl)-3-((S)-1-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one

HRID 1187808Notes

Reaction equation

HRID 1187808 reaction equation
C[C:2]([CH3:36])([CH2:6][C@@:7]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:12][C:11](=[O:13])[N:10]([C@H:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25](=[O:28])[N:24]([CH3:29])[CH:23]=3)=[CH:18][CH:17]=2)[CH3:15])[CH2:9][CH2:8]1)[C:3](N)=O.CC#[N:39].O>>[NH2:39][C:2]([CH3:36])([CH3:3])[CH2:6][C@@:7]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[O:12][C:11](=[O:13])[N:10]([C@H:14]([C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:27]=[CH:26][C:25](=[O:28])[N:24]([CH3:29])[CH:23]=3)=[CH:20][CH:21]=2)[CH3:15])[CH2:9][CH2:8]1

Participants

3

Reactant 2

HCID 18373917Acetonitrile--water (1/1)HCID 596357972,2-dimethyl-3-((R)-3-((S)-1-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl)ethyl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)propanamide

Product 1

HCID 59635681(S)-6-(2-amino-2-methylpropyl)-3-((S)-1-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one

Procedure

A foil covered flask charged with 2,2-dimethyl-3-((R)-3-((S)-1-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl)ethyl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)propanamide (20 mg, 0.04 mmol) in 1:1 CH3CN/H2O (1 mL) was treated with PhI(O2CCF3)2 (31 mg, 0.07 mmol). The reaction was complete after 24 h. The solvent was removed and the crude material purified by prep HPLC to afford (S)-6-(2-amino-2-methylpropyl)-3-((S)-1-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one (16 mg). LC/MS ES+=460 (M+1). LC-MS Method 1 tR=1.06 min, m/z=460 (M+1); 1H NMR (CDCl3) 7.60 (dd, 1H, J=9 Hz, 2Hz), 7.46 (d, 1H, J=3Hz), 7.39-7.27 (m, 5H), 7.20 (d, 2H, J=7Hz), 7.1 (d, 2H, J=8 Hz), 6.78 (d, 1H, J=9Hz, 5.61 (q, 1H, J=7Hz), 3.65 (s, 3H), 2.87 (m, 1H), 2.80 (d, 1H, J=16 Hz), 2.23 (d, 1H, J=16 Hz), 2.19-2.08 (m, 3H), 1.54 (d, 3H, J=7Hz), 1.41 (s, 3H), 0.96 (s, 3H).

Workup

  1. customThe solvent was removed
  2. customthe crude material purified by prep HPLC

Sources & evidence

ORD record
ord-62f8ffc2dc7146aa8ecebe5242eede2b
Source dataset
uspto-grants-2014_03
Patent number
US08673899B2

Reaction notes

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