Hydrochloric Acid → 6-Phenyl-1,3-oxazinan-2-one

HRID 1640791Notes

Reaction equation

HRID 1640791 reaction equation
OC(C)(C)C[C@@:4]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:9][C:8](=[O:10])[N:7]([C@H](C2C=CC(C3C=CN=C(OC)C=3)=CC=2)C)[CH2:6][CH2:5]1.C(=O)([O-])[O-].[K+].[K+].IC.Cl>C(#N)C>[C:27]1([CH:4]2[O:9][C:8](=[O:10])[NH:7][CH2:6][CH2:5]2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59635722(S)-6-(2-hydroxy-2-methylpropyl)-3-((S)-1-(4-(2-methoxypyridin-4-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one

Product 1

HCID 2410056-Phenyl-1,3-oxazinan-2-oneYield 133.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(S)-6-(2-hydroxy-2-methylpropyl)-3-((S)-1-(4-(2-methoxypyridin-4-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one (28 mg, 0.061 mmol), potassium carbonate (17 mg, 2 equiv), and Iodomethane (40 μL, 10 equiv) were mixed with acetonitrile (2.5 mL) and heated at reflux for 4 h. After being cooled to rt, the mixture was acidified with 5% aq HCl and purified by prep HPLC to afford (S)-6-(2-hydroxy-2-methylpropyl)-3-(S)-1-(4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one (14.4 mg. 52%). LC-MS and 1H NMR (CD3OD) were the same as those of product made by Method 1.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 h
  3. custompurified by prep HPLC

Sources & evidence

ORD record
ord-554da03f6aa546dc9c1f3866200fafee
Source dataset
uspto-grants-2012_02
Patent number
US08114868B2

Reaction notes

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