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Ethyl Acetate → Benzyl {1-[5-(3-methylureido)-[1,3,4]oxadiazol-2-yl]-3-phenylpropyl}carbamate

HRID 278037
Notes
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Reaction equation

HRID 278037 reaction equation
[NH2:1][C:2]1[O:6][C:5]([CH:7]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:33][N:34]=[C:35]=[O:36].C(OCC)(=O)C>CS(C)=O>[CH3:33][NH:34][C:35](=[O:36])[NH:1][C:2]1[O:6][C:5]([CH:7]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:4][N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 86757873Benzyl [1-(5-amino-[1,3,4]oxadiazol-2-yl)-3-phenylpropyl]carbamate

Product 1

HCID 86757874Benzyl {1-[5-(3-methylureido)-[1,3,4]oxadiazol-2-yl]-3-phenylpropyl}carbamate

Reagents, catalysts & solvents 1

HCID 679
Dimethyl Sulfoxide
Solvent

Conditions

Temperature
80 °C

Procedure

350 mg of benzyl [1-(5-amino-[1,3,4]oxadiazol-2-yl)-3-phenylpropyl]-carbamate were dissolved in 5 ml of dry dimethyl sulfoxide, treated with 140 mg of potassium carbonate and 140 mg of methyl isocyanate, and stirred at 80° C. for 16 h. The reaction mixture was cooled, treated with ethyl acetate, washed twice with water and once with saturated sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. Benzyl {1-[5-(3-methylureido)-[1,3,4]oxadiazol-2-yl]-3-phenylpropyl}carbamate was obtained, which was employed in the next stage (hydrogenolysis) without further purification.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed twice with water and once with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a45041637cb64bc590a6b503a24fa465
Source dataset
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06358978B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes