p-Toluenesulfonic acid monohydrate → HCID 54136862, compound

HRID 1957032Notes

Reaction equation

HRID 1957032 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[C@H:5]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[O:31][N:30]=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)[N:6]=C(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(#N)C.O>[CH2:1]([O:3][C:4](=[O:32])[C@H:5]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[O:31][N:30]=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)[NH2:6])[CH3:2]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86751784HCID 86751784, compound

Product 1

HCID 54136862HCID 54136862, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Crude N-diphenylmethylene-3-[4-(5-isoxazolyl)-phenyl]-alanine ethyl ester (280 mg) was treated with p-toluenesulfonic acid monohydrate (100 mg) in acetonitrile (35 ml) and water (3,5 ml) at ambient temperature for 3.5 hours. After concentration the residue is extracted with ether and 1N sodium hydroxide, washed with brine, dried concentrated to give crude 3-[4-(5-isoxazolyl)-phenyl]-alanine ethyl ester, which is used for the next step without further purification.

Workup

  1. concentrationAfter concentration the residue
  2. extractionis extracted with ether and 1N sodium hydroxide
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9776e989b7e943af84e2c404be70cbce
Source dataset
uspto-grants-1998_07
Patent number
US05780498

Reaction notes

Loading…