Sodium hydride → HCID 49850061, compound

HRID 1422646Notes

Reaction equation

HRID 1422646 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]([N:13]([CH2:18][CH2:19][C:20]([OH:31])([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:21][C:22]([CH3:24])=[CH2:23])[C:14](=[O:17])OC)([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[H-].[Na+]>C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]([N:13]2[CH2:18][CH2:19][C:20]([CH2:21][C:22]([CH3:24])=[CH2:23])([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[O:31][C:14]2=[O:17])([CH3:12])[CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 66869797HCID 66869797, compound

Product 1

HCID 49850061HCID 49850061, compoundYield 150.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of methyl 4-(4-fluorophenyl)-2-methylbut-3-yn-2-yl(3-hydroxy-5-methyl-3-phenylhex-5-enyl)carbamate (35 mg, 0.03 mmol) in dry THF (2 mL) was added 60% NaH in oil (5 mg, 0.12 mmol). The mixture was heated at 60 C for 3 h, cooled, diluted with EtOAc (90 mL), washed with water (10 mL) and brine (10 mL), and dried over Na2SO4. Removal of the solvent left an oil (18 mg) which was purified by prep HPLC to afford 3-(4-(4-fluorophenyl)-2-methylbut-3-yn-2-yl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one (17.7 mg, 55%) as an oil. LC-MS Method 1 tR=2.22 min, m/z=392; 1H NMR (CDCl3) δ 1.63 (s, 3H), 1.66 (s, 3H), 1.81 (s, 3H), 2.24 (m, 1H), 2.37 (m, 1H), 2.58 (m, 2H), 3.06 (m, 1H), 3.64 (m, 1H), 4.64 (s, 1H), 4.83 (s, 1H), 6.98 (m, 2H), 7.25-7.40 (7H).

Workup

  1. temperatureThe mixture was heated at 60 C for 3 h
  2. temperaturecooled
  3. washwashed with water (10 mL) and brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. customRemoval of the solvent
  6. waitleft an oil (18 mg) which
  7. customwas purified by prep HPLC

Sources & evidence

ORD record
ord-15c92f1000f5485d8b725f2079ecf143
Source dataset
uspto-grants-2015_01
Patent number
US08927539B2

Reaction notes

Loading…