Ethyl Acetate → [5-(3-Methyl-[1,2,4]oxadiazol-5-yl)-4-phenyl-thiazol-2-yl]-carbamic Acid tert-butyl ester

HRID 604488Notes

Reaction equation

HRID 604488 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[N:8][C:7]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O)C.[H-].[Na+].O[NH:28][C:29](=[NH:31])[CH3:30].C(OCC)(=O)C>C1COCC1>[C:15]([O:14][C:12](=[O:13])[NH:11][C:9]1[S:10][C:6]([C:4]2[O:3][N:31]=[C:29]([CH3:30])[N:28]=2)=[C:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:8]=1)([CH3:17])([CH3:18])[CH3:16]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 50742682HCID 50742682, compoundHCID 178465666HCID 178465666, compound

Product 1

HCID 57709599[5-(3-Methyl-[1,2,4]oxadiazol-5-yl)-4-phenyl-thiazol-2-yl]-carbamic Acid tert-butyl esterYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Tert-butoxycarbonylamino-4-phenyl-thiazole-5-carboxylic acid ethyl ester (1.9 g 5.6 mmol) was dissolved in dry THF (60 mL). Sodium hydride (60% in oil) and N-hydroxy-acetamidine (0.83 g, 11.2 mmol) dissolved in THF (30 mL) was added. The reaction mixture was heated to reflux over night. The reaction mixture was cooled and ethyl acetate (75 mL) glacial acetic acid (0.43 g) were added. The organic mixture was washed with brine (75 mL). The aqueous phase was extracted with ethylacetate The combined organic phases was washed with brine (50 mL) dried with MgSO4 and solvents were removed in vacuo to give a solid. Yield: 36%.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux over night
  4. temperatureThe reaction mixture was cooled
  5. washThe organic mixture was washed with brine (75 mL)
  6. extractionThe aqueous phase was extracted with ethylacetate The combined organic phases
  7. washwas washed with brine (50 mL)
  8. dry with materialdried with MgSO4 and solvents
  9. customwere removed in vacuo
  10. customto give a solid

Sources & evidence

ORD record
ord-1fc7453889f240fc94996d1a9dc9328a
Source dataset
uspto-grants-2011_03
Patent number
US07910613B2

Reaction notes

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