HCID 69939868, compound → HCID 57221532, compound

HRID 1058963Notes

Reaction equation

HRID 1058963 reaction equation
CO[C:3](=[O:18])[CH2:4][NH:5][C:6](=[O:17])[C@@H:7]([NH:15][CH3:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[CH3:16][N:15]1[C@@H:7]([CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:6](=[O:17])[NH:5][CH2:4][C:3]1=[O:18]

Participants

3

Reactant 1

HCID 69939868HCID 69939868, compound

Product 1

HCID 57221532HCID 57221532, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (S)-N-[2-(methylamino)-1-oxo-3-phenylpropyl)glycine methyl ester (Description 33, 1.59 g, 6.4 mmol) in toluene (15 mL) was heated at 170° C. in a sealed tube for 42 h. The mixture was cooled, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2/MeOH/NH3(aq.) (95:5:1), to give the title compound as a colorless solid (1.19 g, 86%). 1H NMR (360 MHz, CDCl3) δ7.31 (3H, m), 7.14 (2H, m), 5.93 (1H, br s), 4.16 (1H, m), 3.44 (1H, dd, J 17.0, 3.6 Hz), 3.27 (1H, dd, J 13.9, 3.7 Hz), 3.16 (1H, dd, J 13.9, 4.6 Hz), 3.06 (3H, s), and 2.48 (1H, d, J 17.0 Hz). mI/z (ES+) 218 (M+1).

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent was evaporated under reduced pressure
  3. customthe residue was purified by flash column chromatography on silica gel
  4. washeluting with CH2Cl2/MeOH/NH3(aq.) (95:5:1)

Sources & evidence

ORD record
ord-01ccb5e3a4da470a833eac1582d1260e
Source dataset
uspto-grants-2003_02
Patent number
US06518273B1

Reaction notes

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