Nitrogen → [2-(3-Acetyl-benzyl)-oxazol-4-yl]-[2-(4-trifluoromethyl-phenyl)-vinyl]-carbamic acid tert-butyl ester

HRID 1189417Notes

Reaction equation

HRID 1189417 reaction equation
N#N.[C:3]([O:7][C:8](=[O:25])[NH:9][C:10]1[N:11]=[C:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22](=[O:24])[CH3:23])[CH:17]=2)[O:13][CH:14]=1)([CH3:6])([CH3:5])[CH3:4].[H-].[Na+].[F:28][C:29]([F:42])([F:41])[C:30]1[CH:35]=[CH:34][C:33]([CH:36]=[CH:37]C(Cl)=O)=[CH:32][CH:31]=1>C1COCC1.O>[C:3]([O:7][C:8](=[O:25])[N:9]([C:10]1[N:11]=[C:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22](=[O:24])[CH3:23])[CH:17]=2)[O:13][CH:14]=1)[CH:37]=[CH:36][C:33]1[CH:32]=[CH:31][C:30]([C:29]([F:28])([F:41])[F:42])=[CH:35][CH:34]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 947NitrogenHCID 24758Sodium hydrideHCID 542691863-[4-(Trifluoromethyl)phenyl]prop-2-enoyl chlorideHCID 67128654[2-(3-Acetyl-benzyl)-oxazol-4-yl]-carbamic acid tert-butyl ester

Product 1

HCID 67128870[2-(3-Acetyl-benzyl)-oxazol-4-yl]-[2-(4-trifluoromethyl-phenyl)-vinyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [2-(3-acetyl-benzyl)-oxazol-4-yl]-carbamic acid tert-butyl ester (15 mg, 0.05 mmol) in THF (1.0 mL) was added to a suspension of NaH (5 mg, 0.12 mmol) in THF (0.5 mL) at 0° C. The resulting suspension was stirred at 0° C. for 5 min and at rt for 30 min. It was cooled to 0° C. and treated dropwise with a solution of the above prepared 3-(4-trifluoromethyl-phenyl)-acryloyl chloride in THF (1.0 mL). The resulting suspension was stirred for 5 min at 0° C. followed by 30 min at rt. Water was then added and the aq. layer was extracted several time with EA. The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to give the title compound as a yellow oil. TLC: rf (6:4 hept-EA)=0.20. LC-MS-conditions 02: tR=1.17 min, [M+H]+=515.82.

Workup

  1. temperatureIt was cooled to 0° C.
  2. additiontreated dropwise with a solution of the
  3. stirringThe resulting suspension was stirred for 5 min at 0° C.
  4. waitfollowed by 30 min at rt
  5. extractionthe aq. layer was extracted several time with EA
  6. dry with materialextracts were dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-04878a1df227422ea631cff0f0c37e24
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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