Nitrogen → (2-Methyl-5-m-tolyl-oxazole-4-carbonyl)-[2-(5-oxo-hexyl)-oxazol-4-yl]-carbamic acid tert-butyl ester

HRID 1189378Notes

Reaction equation

HRID 1189378 reaction equation
N#N.[C:3]([O:7][C:8](=[O:22])[NH:9][C:10]1[N:11]=[C:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:21])[CH3:20])[O:13][CH:14]=1)([CH3:6])([CH3:5])[CH3:4].[H-].[Na+].[CH3:25][C:26]1[O:27][C:28]([C:34]2[CH:35]=[C:36]([CH3:40])[CH:37]=[CH:38][CH:39]=2)=[C:29]([C:31](Cl)=[O:32])[N:30]=1>C1COCC1.O>[C:3]([O:7][C:8](=[O:22])[N:9]([C:31]([C:29]1[N:30]=[C:26]([CH3:25])[O:27][C:28]=1[C:34]1[CH:35]=[C:36]([CH3:40])[CH:37]=[CH:38][CH:39]=1)=[O:32])[C:10]1[N:11]=[C:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:21])[CH3:20])[O:13][CH:14]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 947NitrogenHCID 24758Sodium hydrideHCID 67128525[2-(5-Oxo-hexyl)-oxazol-4-yl]-carbamic acid tert-butyl esterHCID 866649052-Methyl-5-m-tolyl-oxazole-4-carbonyl chloride

Product 1

HCID 67128523(2-Methyl-5-m-tolyl-oxazole-4-carbonyl)-[2-(5-oxo-hexyl)-oxazol-4-yl]-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-(5-oxo-hexyl)-oxazol-4-yl]-carbamic acid tert-butyl ester (50 mg, 0.18 mL) in THF (1.0 mL) was added to a suspension of NaH (19 mg, 0.43 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 2-methyl-5-m-tolyl-oxazole-4-carbonyl chloride in THF (1.0 mL). The resulting suspension was stirred for 30 min at 0° C. followed by 2 h 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. Purification of the residue by FC (1:1 hept-EA) gave the title compound as a pale yellow oil. TLC: rf (1:1 hept-EA)=0.32. LC-MS-conditions 02: tR=1.10 min, [M+H]+=482.06.

Workup

  1. temperatureIt was cooled to 0° C.
  2. additiontreated dropwise with a solution of the
  3. stirringThe resulting suspension was stirred for 30 min at 0° C.
  4. waitfollowed by 2 h 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
  9. customPurification of the residue by FC (1:1 hept-EA)

Sources & evidence

ORD record
ord-d0bf782764fc45deb156dfd2c81295f4
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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