Potassium Carbonate → HCID 58739188, compound

HRID 720261Notes

Reaction equation

HRID 720261 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=O)[CH:11]=1)[CH3:9])(C)(C)C.S([CH2:29][N+:30]#[C-])(C1C=CC(C)=CC=1)(=O)=O.[C:32](=[O:35])([O-])[O-].[K+].[K+]>C(O)C>[O:35]1[CH:32]=[C:16]([C:12]2[CH:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[CH:15]=[CH:14][CH:13]=2)[N:30]=[CH:29]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 58739156HCID 58739156, compound

Product 1

HCID 58739188HCID 58739188, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S)-[1-(3-formyl-phenyl)-ethyl]-carbamic acid tert-butyl ester (500 mg, 2 mmol) and tosylmethylisocyanide (391 g, 2 mmol) in ethanol (5 mL) was added potassium carbonate (277 mg, 2 mmol), and the reaction mixture was heated at reflux for 24 h. The reaction mixture was cooled down to room temperature and filtered. The filtrate was evaporated in vacuo, and the residue was purified by preparative HPLC (5 mM NH4OAc buffer; gradient 0% to 100% B in 10 min (A: 10 % CH3CN/H2O, B: 90% CH3CN/H2O); column: YMC 20×100 mm C-18 ) to provide the title compound (280 mg, 48% yield) as a brown oil.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 24 h
  3. filtrationfiltered
  4. customThe filtrate was evaporated in vacuo
  5. customthe residue was purified by preparative HPLC (5 mM NH4OAc buffer

Sources & evidence

ORD record
ord-3e649e0f52044a3ebc44e954e8d161a8
Source dataset
uspto-grants-2006_11
Patent number
US07135472B2

Reaction notes

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