Potassium Carbonate → tert-butyl [(1S)-2-({1-[6-(2-cyclopropylethoxy)-1,3-benzoxazol-2-yl]piperidin-4-yl}oxy)-1-methylethyl]carbamate

HRID 2368119Notes

Reaction equation

HRID 2368119 reaction equation
[CH:1]1([CH2:4][CH2:5][OH:6])[CH2:3][CH2:2]1.CS(Cl)(=O)=O.O[C:13]1[CH:39]=[CH:38][C:16]2[N:17]=[C:18]([N:20]3[CH2:25][CH2:24][CH:23]([O:26][CH2:27][C@@H:28]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH3:29])[CH2:22][CH2:21]3)[O:19][C:15]=2[CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[CH:1]1([CH2:4][CH2:5][O:6][C:13]2[CH:39]=[CH:38][C:16]3[N:17]=[C:18]([N:20]4[CH2:25][CH2:24][CH:23]([O:26][CH2:27][C@@H:28]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[CH3:29])[CH2:22][CH2:21]4)[O:19][C:15]=3[CH:14]=2)[CH2:3][CH2:2]1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 1376422-Cyclopropylethan-1-olHCID 86658692tert-butyl [(1S)-2-{[1-(6-hydroxy-1,3-benzoxazol-2-yl)piperidin-4-yl]oxy}-1-methylethyl]carbamate

Product 1

HCID 86658707tert-butyl [(1S)-2-({1-[6-(2-cyclopropylethoxy)-1,3-benzoxazol-2-yl]piperidin-4-yl}oxy)-1-methylethyl]carbamateYield 64.7%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-cyclopropylethanol (550 mg) in THF (10 mL) were added triethylamine (0.80 mL) and methanesulfonyl chloride (0.50 mL), and the mixture was stirred at room temperature for 30 min. The reaction mixture was added to a suspension of tert-butyl [(1S)-2-{[1-(6-hydroxy-1,3-benzoxazol-2-yl)piperidin-4-yl]oxy}-1-methylethyl]carbamate (250 mg) and potassium carbonate (1.8 g) in DMF (10 mL), and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (190 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 15 hr
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-59c8b7366b874bbdaebd2bf7df6eacb3
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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