Potassium Carbonate → Tert-butyl (5-(((2-(4-(benzyloxy)phenyl)cyclopropyl)amino)methyl)-1,3,4-oxadiazol-2-yl)carbamate

HRID 709419Notes

Reaction equation

HRID 709419 reaction equation
Cl[CH2:2][C:3]1[O:7][C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:5][N:4]=1.[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]2[CH2:32][CH:31]2[NH2:33])=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:16]([O:23][C:24]1[CH:25]=[CH:26][C:27]([CH:30]2[CH2:32][CH:31]2[NH:33][CH2:2][C:3]2[O:7][C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:5][N:4]=2)=[CH:28][CH:29]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 438103422-[4-(Benzyloxy)phenyl]cyclopropan-1-amineHCID 86695279Tert-butyl (5-(chloromethyl)-1,3,4-oxadiazol-2-yl)carbamate

Product 1

HCID 66715786Tert-butyl (5-(((2-(4-(benzyloxy)phenyl)cyclopropyl)amino)methyl)-1,3,4-oxadiazol-2-yl)carbamateYield 37.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Tert-butyl (5-(chloromethyl)-1,3,4-oxadiazol-2-yl)carbamate (141 mg, 0.606 mmol) was added to a solution of 2-(4-(benzyloxy)phenyl)cyclopropanamine (enantiomer (−)) (145 mg, 0.606 mmol) and K2CO3 (166 mg, 1.213 mmol) in dry DMF (1.5 mL) and stirred at RT for 2 h. After completion, the reaction mixture was poured into ice water (10 mL) and extracted with EtOAc (4×10 mL). The combined organic extracts were washed with water (3×10 mL), brine (10 mL), dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The residue obtained was purified by column chromatography (SiO2) using MeOH:CHCl3 (1:99) as eluent to afford tert-butyl (5-(((2-(4-(benzyloxy)phenyl)cyclopropyl)amino)methyl)-1,3,4-oxadiazol-2-yl)carbamate (enantiomer-(−)) (100 mg, 37.7%) as a pale green liquid.

Workup

  1. extractionextracted with EtOAc (4×10 mL)
  2. washThe combined organic extracts were washed with water (3×10 mL), brine (10 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue obtained
  7. customwas purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-2d598d9143654cd397c7e6224ea62869
Source dataset
uspto-grants-2015_11
Patent number
US09181198B2

Reaction notes

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