Sodium Hydroxide → HCID 59532389, compound

HRID 1191774Notes

Reaction equation

HRID 1191774 reaction equation
N[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C@@H:14]([N:16]3[CH2:21][CH2:20][C@:19]([CH2:28][CH2:29][CH2:30][OH:31])([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[O:18][C:17]3=[O:32])[CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.N([O-])=[O:34].[Na+].[OH-].[Na+]>OS(O)(=O)=O>[OH:31][CH2:30][CH2:29][CH2:28][C@@:19]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:18][C:17](=[O:32])[N:16]([C@H:14]([C:11]2[CH:10]=[CH:9][C:8]([C:5]3[CH:4]=[CH:3][C:2](=[O:34])[NH:7][CH:6]=3)=[CH:13][CH:12]=2)[CH3:15])[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 59532371HCID 59532371, compound

Product 1

HCID 59532389HCID 59532389, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

(R)-3-((S)-1-(4-(6-aminopyridin-3-yl)phenyl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one (40 mg, 0.09 mmol.) was dissolved in 3.5 M H2SO4 (10 mL), and 2 M NaNO2 (10 mL) was added at 0° C. The reaction mixture was stirred at rt for 2 h and treated with NaOH solution. The mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, and concentrated to afford the residue, which was purified by preparative HPLC to give (R)-6-(3-hydroxypropyl)-3-((S)-1-(4-(6-oxo-1,6-dihydropyridin-3-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one (10 mg, 20%). LC-MS Method 2 tR=1.66, min, m/z=433, 455; 1H NMR (CDCl3): 1.36 (m, 2H), 1.50 (m, 3H), 1.68 (m, 2H), 1.92 (m, 2H), 2.10-2.30 (m, 3H), 2.84 (m, 1H), 3.50 (m, 2H), 5.12 (m, 1H), 6.62 (m, 1H), 6.86 (m, 2H), 7.08 (m, 2H), 7.18-7.32 (m, 5H), 7.46 (m, 1H), 7.62 (m, 1H).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customto afford the residue, which
  6. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-8242ffe8d3124fd2b4729c488ebddd57
Source dataset
uspto-grants-2014_03
Patent number
US08680093B2

Reaction notes

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