p-Toluenesulfonic acid monohydrate → HCID 11644199, compound

HRID 15392Notes

Reaction equation

HRID 15392 reaction equation
[O:1]=[C:2](C)[C:3]([NH:5][C:6](=[O:16])[C@H:7]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH2:8])=O.[CH3:18]C1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH2:9]([C@@H:7]1[NH:8][C:2](=[O:1])[C:3](=[CH2:18])[NH:5][C:6]1=[O:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86608543N-2-oxo-propanoyl-L-phenylalanine amide

Product 1

HCID 11644199HCID 11644199, compoundYield 1,789.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Using a Dean-Stark trap whose trap part was filled with molecular sieves 3A, a solution of N-2-oxo-propanoyl-L-phenylalanine amide from Example 1a (100 mg, 0.427 mmol) in toluene (20 mL) was refluxed in the presence of p-TsOH.H2O (4.37 mg, 0.023 mmol, 0.05 eq) for 18 h. After removal of the solvent, the residue was triturated in ether to obtain 89 mg (96%) of the title compound as a white solid: mp 175-177° C. (decomp); 1H NMR (300 MHz, DMSO-d6) δ 10.36 (s, 1H), 8.41 (s, 1H), 7.24-7.11 (m, 5H), 4.90 (s, 1H), 4.50 (s, 1H), 4.40-4.37 (m, 1H), 3.15 (dd, J=3.8, 13.5 Hz, 1H), 2.91 (dd, J=5.0, 13.5 Hz, 1H); HRMS (EI): m/z 216.0891(M+) (calcd for C12H12N2O2: 216.0899). Enantiomeric excess was determined to be >99% using chiral HPLC with a CHIRALCEL OD column.

Workup

  1. customAfter removal of the solvent
  2. customthe residue was triturated in ether

Sources & evidence

ORD record
ord-67a8b3451a3e4caf979b66d22bde943b
Source dataset
uspto-grants-2010_06
Patent number
US07732605B2

Reaction notes

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