Sodium hydride → 6-(2-methylallyl)-6-phenyl-3-(2-(1-phenyl-1H-1,2,3-triazol-4-yl)propan-2-yl)-1,3-oxazinan-2-one

HRID 1422650Notes

Reaction equation

HRID 1422650 reaction equation
[OH:1][C:2]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([CH2:24][C:25]([CH3:27])=[CH2:26])[CH2:3][CH2:4][N:5]([C:10]([C:13]1[N:14]=[N:15][N:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:17]=1)([CH3:12])[CH3:11])[C:6](=O)[O:7]C.[H-].[Na+]>C1COCC1.Cl.CO>[CH3:27][C:25](=[CH2:26])[CH2:24][C:2]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:1][C:6](=[O:7])[N:5]([C:10]([C:13]2[N:14]=[N:15][N:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:17]=2)([CH3:11])[CH3:12])[CH2:4][CH2:3]1

Participants

6

Reactant 2

HCID 24758Sodium hydrideHCID 68160533methyl 3-hydroxy-5-methyl-3-phenylhex-5-enyl(2-(1-phenyl-1H-1,2,3-triazol-4-yl)propan-2-yl)carbamate

Product 1

HCID 509057376-(2-methylallyl)-6-phenyl-3-(2-(1-phenyl-1H-1,2,3-triazol-4-yl)propan-2-yl)-1,3-oxazinan-2-oneYield 67.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3-hydroxy-5-methyl-3-phenylhex-5-enyl(2-(1-phenyl-1H-1,2,3-triazol-4-yl)propan-2-yl)carbamate (14 mg, 0.031 mmol) in dry THF (1 mL) was added 60% NaH in oil (10 mg, 0.25 mmol). The mixture was heated at 50 C in an oil bath for 1.5 h, cooled, diluted with 5% aq HCl (0.5 mL) and MeOH (0.5 mL) and purified by prep HPLC to afford the title compound (8.7 mg, 67%) as an oil. LC-MS Method 1 tR=1.90 min, m/z=417; 1H NMR (CDCl3) 1.58 (s, 3H), 1.76 (s, 6H), 2.25 (m, 1H), 2.36 (m, 1H), 2.56 (dd, 2H), 3.03 (m, 1H), 3.52 (m, 1H), 4.58 (s, 1H), 4.81 (s, 1H), 7.25-7.80 (11H).

Workup

  1. temperatureThe mixture was heated at 50 C in an oil bath for 1.5 h
  2. temperaturecooled
  3. custompurified by prep HPLC

Sources & evidence

ORD record
ord-9560ee898c914b6d86c0b5dac4920378
Source dataset
uspto-grants-2015_01
Patent number
US08927539B2

Reaction notes

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