tert-Butanol → HCID 86655408, compound

HRID 2190487Notes

Reaction equation

HRID 2190487 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[O:8][C:9]3[CH:15]=[C:14]([O:16][C:17]4[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=4)C(O)=O)[CH:13]=[CH:12][C:10]=3[N:11]=2)=[O:5])[CH2:3][CH2:2]1.C([N:28]([CH:32](C)C)C(C)C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:42])C=CC=CC=1.[CH3:52][C:53]([OH:56])([CH3:55])[CH3:54]>O1CCCC1>[CH:1]1([C:4]([NH:6][C:7]2[O:8][C:9]3[CH:15]=[C:14]([O:16][C:17]4[CH:18]=[C:19]([NH:28][C:32](=[O:42])[O:56][C:53]([CH3:55])([CH3:54])[CH3:52])[CH:23]=[CH:24][CH:25]=4)[CH:13]=[CH:12][C:10]=3[N:11]=2)=[O:5])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 67312850HCID 67312850, compound

Product 1

HCID 86655408HCID 86655408, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-({2-[(cyclopropylcarbonyl)amino]-1,3-benzooxazol-6-yl}oxy)benzoic acid (8.6 g) in tetrahydrofuran (100 mL) and 2-methylpropan-2-ol (50 mL) were added N-ethyl-N-isopropylpropane-2-amine (20 L, 115 mmol) and diphenylphosphoryl azide (22 mL, 102 mmol), and the mixture was heated under reflux for 6 hr. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (250 mL), and the mixture was washed with saturated aqueous sodium hydrogencarbonate solution (100 mL×2) and saturated brine (100 mL), successively, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/98→80/20) to give the objective tert-butyl [3-({2-[(cyclopropylcarbonyl)amino]-1,3-benzooxazol-6-yl}oxy)phenyl]carbamate as a brown amorphous substance (3.25 g). The obtained compound was used in the next operation without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hr
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate (250 mL)
  5. washthe mixture was washed with saturated aqueous sodium hydrogencarbonate solution (100 mL×2) and saturated brine (100 mL)
  6. dry with materialsuccessively, and dried over anhydrous magnesium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/98→80/20)

Sources & evidence

ORD record
ord-964f62e0ae4d4362837d875ea600b3c9
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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