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

HRID 1189432Notes

Reaction equation

HRID 1189432 reaction equation
N#N.C(OC(=O)[N:9]([C:23]1[N:24]=[C:25]([CH2:28][CH2:29][CH2:30][CH2:31][C:32](=[O:34])[CH3:33])[O:26][CH:27]=1)[C:10]([C:12]1[N:13]=[CH:14][O:15][C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:11])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[O:34]=[C:32]([CH3:33])[CH2:31][CH2:30][CH2:29][CH2:28][C:25]1[O:26][CH:27]=[C:23]([NH:9][C:10]([C:12]2[N:13]=[CH:14][O:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:11])[N:24]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 6422Trifluoroacetic acidHCID 67128650[2-(5-Oxo-hexyl)-oxazol-4-yl]-(5-phenyl-oxazole-4-carbonyl)-carbamic acid tert-butyl ester

Product 1

HCID 498397725-Phenyl-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-(5-oxo-hexyl)-oxazol-4-yl]-(5-phenyl-oxazole-4-carbonyl)-carbamic acid tert-butyl ester (31 mg, 0.06 mmol) in dry CH2Cl2 (1.0 mL) was treated at 0° C. with trifluoroacetic acid (0.05 mL, 0.64 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 light brown solid. TLC: rf (1:1 hept-EA)=0.35. LC-MS-conditions 02: tR=1.02 min, [M+H]+=354.25.

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-211ed6786d01458e905e721a93312479
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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