Nitrogen → 2-Methyl-5-m-tolyl-oxazole-4-carboxylic acid [2-(5-oxo-hexyl)-oxazol-4-yl]-amide

HRID 1189434Notes

Reaction equation

HRID 1189434 reaction equation
N#N.C(OC(=O)[N:9]([C:22]([C:24]1[N:25]=[C:26]([CH3:36])[O:27][C:28]=1[C:29]1[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=1)=[O:23])[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)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[O:21]=[C:19]([CH3:20])[CH2:18][CH2:17][CH2:16][CH2:15][C:12]1[O:13][CH:14]=[C:10]([NH:9][C:22]([C:24]2[N:25]=[C:26]([CH3:36])[O:27][C:28]=2[C:29]2[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=2)=[O:23])[N:11]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 6422Trifluoroacetic acidHCID 67128523(2-Methyl-5-m-tolyl-oxazole-4-carbonyl)-[2-(5-oxo-hexyl)-oxazol-4-yl]-carbamic acid tert-butyl ester

Product 1

HCID 498398912-Methyl-5-m-tolyl-oxazole-4-carboxylic acid [2-(5-oxo-hexyl)-oxazol-4-yl]-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of (2-methyl-5-m-tolyl-oxazole-4-carbonyl)-[2-(5-oxo-hexyl)-oxazol-4-yl]-carbamic acid tert-butyl ester (50 mg, 0.10 mmol) in dry CH2Cl2 (1.0 mL) was treated at 0° C. with trifluoroacetic acid (0.08 mL, 1.07 mmol). After stirring at rt for 16 h, the reaction mixture was quenched with sat. aq. NaHCO3, extracted with CH2Cl2 (3×10 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by HPLC gave the title compound as a colorless oil. TLC: rf (6:4 hept-EA)=0.26. LC-MS-conditions 02: tR=1.08 min, [M+H]+=382.50.

Workup

  1. customthe reaction mixture was quenched with sat. aq. NaHCO3
  2. extractionextracted with CH2Cl2 (3×10 mL)
  3. dry with materialextracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by HPLC

Sources & evidence

ORD record
ord-d78d3475f9f34815a9e6016b4802feec
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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