Potassium Carbonate → tert-butyl [(1S)-2-({5-[5-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]isoxazol-3-yl}oxy)-1-methylethyl]carbamate

HRID 1026210Notes

Reaction equation

HRID 1026210 reaction equation
Br[CH2:2][CH:3]1[CH2:5][CH2:4]1.[OH:6][C:7]1[CH:8]=[CH:9][C:10]2[O:14][C:13]([C:15]3[O:19][N:18]=[C:17]([O:20][CH2:21][C@@H:22]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH3:23])[CH:16]=3)=[N:12][C:11]=2[CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:5]1([CH2:4][O:6][C:7]2[CH:8]=[CH:9][C:10]3[O:14][C:13]([C:15]4[O:19][N:18]=[C:17]([O:20][CH2:21][C@@H:22]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])[CH3:23])[CH:16]=4)=[N:12][C:11]=3[CH:32]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 86666264tert-butyl [(1S)-2-{[5-(5-hydroxy-1,3-benzoxazol-2-yl)isoxazol-3-yl]oxy}-1-methylethyl]carbamate

Product 1

HCID 86666265tert-butyl [(1S)-2-({5-[5-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]isoxazol-3-yl}oxy)-1-methylethyl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

(Bromomethyl)cyclopropane (0.388 mL) was added to a mixture of tert-butyl [(1S)-2-{[5-(5-hydroxy-1,3-benzoxazol-2-yl)isoxazol-3-yl]oxy}-1-methylethyl]carbamate (500 mg), potassium carbonate (552 mg) and DMF (13 mL), and the mixture was stirred at 60° C. for 5 hr. The solvent was evaporated under reduced pressure, water was added thereto, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with hexane-ethyl acetate to give the title compound (510 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure, water
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe combined organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. washThe residue was washed with hexane-ethyl acetate

Sources & evidence

ORD record
ord-39b075510d5b46edb8467e799a768d12
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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