p-Toluenesulfonic acid monohydrate → HCID 11950450, compound

HRID 15393Notes

Reaction equation

HRID 15393 reaction equation
[CH2:1]([NH:8][C:9](=[O:24])[C@H:10]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH:11][C:12](=[O:16])[C:13](=O)[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[C:13](=[CH2:14])[C:12](=[O:16])[NH:11][C@@H:10]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 11950627N-2-oxo-propanoyl-L-phenylalanine benzylamide

Product 1

HCID 11950450HCID 11950450, compoundYield 53%

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 benzylamide from Example 3a (100 mg, 0.31 mmol) in toluene (20 mL) was refluxed in the presence of p-TsOH.H2O (1.8 mg, 0.0093 mmol, 0.03 eq) for 24 h. After removal of the solvent, the residue was purified by a silica gel chromatography to yield 50 mg (53%) of title compound as a white solid: mp 124-127° C., 1H NMR (300 MHz, CDCl3) δ 7.01-7.35 (m, 10H), 6.84 (br s, 1H), 5.60 (s, 1H), 5.01 (d, J=15.7 Hz, 1H), 4.85 (d, J=15.7 Hz, 1H), 4.76 (s, 1H), 4.49-4.52 (m, 1H), 3.36 (dd, J=3.7, 13.6 Hz, 1H), 3.12 (dd, J=7.7, 13.6 Hz, 1H); HRMS (EI): m/z 306.1369 (M+) (calcd for C19H18N2O2: 306.1368). 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 purified by a silica gel chromatography

Sources & evidence

ORD record
ord-9a416754de904acf9d7841ce5e9a3158
Source dataset
uspto-grants-2010_06
Patent number
US07732605B2

Reaction notes

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