2-[2-Oxo-2-[[(1S)-1-phenylpropyl]amino]ethyl]benzoic acid → HCID 57733384, compound

HRID 1920749Notes

Reaction equation

HRID 1920749 reaction equation
[C:1]1([C@@H:7]([NH:10][C:11]([CH2:13][C:14]2[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=2[C:16]([OH:18])=[O:17])=[O:12])[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(OC(=O)CC)(=O)CC>[O:12]=[C:11]([CH2:13][CH3:14])[CH:13]([C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17])[C:11](=[O:12])[NH:10][C@H:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:8][CH3:9]

Participants

3

Reactant 1

HCID 577332512-[2-Oxo-2-[[(1S)-1-phenylpropyl]amino]ethyl]benzoic acid

Product 1

HCID 57733384HCID 57733384, compound

Reagents, catalysts & solvents 1

HCID 31263Propionic anhydrideSolvent

Conditions

Temperature
150 °C

Procedure

A sealed mixture of 2-[((S)-1-phenyl-propylcarbamoyl)-methyl]-benzoic acid (409 mg, 1.38 mmol), propionic anhydride (10 ml) and 4-N,N-dimethylaminopyridine (15 mg) was heated under microwave irradiation at 150° C. for 20 min and partitioned between 1M HCl (50 ml) and ethyl acetate (100 ml). The organic layer was washed with sat. aq. NaHCO3 (2×50 ml) and brine and concentrated in vacuo. To the obtained residue methanol (25 ml) tetrahydrofurane (25 ml) and 2M aq. NaOH (50 ml) was added and stirred at r.t. for 1 hour. The organic volatiles were removed in vacuo and the pH was adjusted to 1 with 3M aq. HCl. The crude title product (495 mg) was separated by extraction with ethyl acetate (150 ml) and used in the next step without further purification. 1H NMR (500 MHz, DMSO-d6): a mixture of tautomers and diastereoisomers.

Workup

  1. custompartitioned between 1M HCl (50 ml) and ethyl acetate (100 ml)
  2. washThe organic layer was washed with sat. aq. NaHCO3 (2×50 ml) and brine
  3. concentrationconcentrated in vacuo
  4. additionTo the obtained residue methanol (25 ml) tetrahydrofurane (25 ml) and 2M aq. NaOH (50 ml) was added
  5. customThe organic volatiles were removed in vacuo
  6. customThe crude title product (495 mg) was separated by extraction with ethyl acetate (150 ml)
  7. customused in the next step without further purification
  8. addition1H NMR (500 MHz, DMSO-d6): a mixture of tautomers and diastereoisomers

Sources & evidence

ORD record
ord-18b42d4c3476440f852a7ffae024744d
Source dataset
uspto-grants-2012_05
Patent number
US08173639B2

Reaction notes

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