Nitrogen → [2-(5-Acetyl-furan-2-ylmethyl)-thiazol-4-yl]-carbamic acid tert-butyl ester

HRID 1189430Notes

Reaction equation

HRID 1189430 reaction equation
N#N.[C:3]([C:6]1[O:10][C:9]([CH2:11][C:12]2[S:13][CH:14]=[C:15](C(O)=O)[N:16]=2)=[CH:8][CH:7]=1)(=[O:5])[CH3:4].CC[N:22](CC)CC.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.[C:44]([O-:47])(O)=[O:45].[Na+].[C:49]1([CH3:55])[CH:54]=CC=C[CH:50]=1>C(O)(C)(C)C.CC(=O)OCC>[C:49]([O:47][C:44](=[O:45])[NH:22][C:15]1[N:16]=[C:12]([CH2:11][C:9]2[O:10][C:6]([C:3](=[O:5])[CH3:4])=[CH:7][CH:8]=2)[S:13][CH:14]=1)([CH3:55])([CH3:54])[CH3:50]

Participants

9

Reactant 6

HCID 947NitrogenHCID 1140TolueneHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 671284572-(5-Acetyl-furan-2-ylmethyl)-thiazole-4-carboxylic acid

Product 1

HCID 67128535[2-(5-Acetyl-furan-2-ylmethyl)-thiazol-4-yl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-(5-acetyl-furan-2-ylmethyl)-thiazole-4-carboxylic acid (1.00 g, 3.98 mmol) in a mixture of toluene (10.8 mL) and t-butanol (5.6 mL) was treated at rt with Et3N (0.64 mL, 4.58 mmol) and DPPA (0.90 mL, 4.18 mmol). After stirring at rt for 5 min, the reaction mixture was stirred at 90° C. for 2 h. Cuprous chloride (61 mg, 0.60 mmol) was then added and the reaction mixture was stirred under reflux for 1 h. The reaction was allowed to cool down to rt and EA (50 mL) was added followed by NaHCO3 (50 mL). The aq. layer was extracted twice with EA (50 mL) and the combined org. layers were washed with brine (100 mL), dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (6:4 hept-EA) gave the title compound as an orange oil. TLC: rf (6:4 hept-EA)=0.32. LC-MS-conditions 02: tR=0.97 min, [M+H]+=323.37.

Workup

  1. stirringthe reaction mixture was stirred at 90° C. for 2 h
  2. stirringthe reaction mixture was stirred
  3. temperatureunder reflux for 1 h
  4. temperatureto cool down to rt
  5. extractionThe aq. layer was extracted twice with EA (50 mL)
  6. washlayers were washed with brine (100 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe solvent was removed under reduced pressure
  10. customPurification of the residue by FC (6:4 hept-EA)

Sources & evidence

ORD record
ord-1e8be38961cd4b0d9800a47c57099cd5
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

Loading…