Hydrazine → (s)-2-Phenyl-1-(5-phenyloxazol-2-yl)ethanamine

HRID 1524860Notes

Reaction equation

HRID 1524860 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[C@@H:12]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]([NH:15][CH2:16][C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O.NN>CCO>[C:26]1([CH2:25][C@@H:12]([C:13]2[O:24][C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][N:15]=2)[NH2:3])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 66674794(s)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-n-(2-oxo-2-phenyl-ethyl)-3-phenyl-propionamide

Product 1

HCID 42048374(s)-2-Phenyl-1-(5-phenyloxazol-2-yl)ethanamineYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product from Example 48 Part B (160 mg, 0.4 mmol) in EtOH (10 mL) was added to hydrazine (39 mg, 1.2 mmol). The reaction mixture was refluxed for 2 h. It was cooled to rt. EtOH was removed under vacuum. The residue was re-dissolved in dichloromethane. The undissolved solid was removed by filtration. The filtrate was concentrated to yield 95 mg of the product as a yellow solid (90% yield). MS 265.1 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. customEtOH was removed under vacuum
  3. dissolutionThe residue was re-dissolved in dichloromethane
  4. customThe undissolved solid was removed by filtration
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1fbc486fe9c2486ca8024229b616c280
Source dataset
uspto-grants-2015_07
Patent number
US09079860B2

Reaction notes

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