p-Toluenesulfonic acid → 1501-32-2

HRID 1899951Notes

Reaction equation

HRID 1899951 reaction equation
C[O:2][C:3](=O)[CH:4]([CH2:15][CH2:16][C:17]([O:19]C)=O)[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.[Pd]>[C:17]1(=[O:19])[N:5]2[C:6]3[C:7]([NH:12][C:3](=[O:2])[CH:4]2[CH2:15][CH2:16]1)=[CH:8][CH:9]=[CH:10][CH:11]=3

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 10357193HCID 10357193, compound

Product 1

HCID 2581141501-32-2

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To N-(2-nitrophenyl)-DL-glutamic acid dimethyl ester (XI, EXAMPLE 279, 5.09 g) in methanol (150 ml) is added p-toluenesulfonic acid (0.158 g) and palladium on carbon (10%, 0.495 g). The mixture is shaken under hydrogen at 37 psi for 2 hr; the mixture is then filtered and the tiltrate is concentrated to about 70 ml. Additional p-toluenesulfonic acid (0.15 g) is added, and the solution is heated at 60° for 1 hr. After cooling, the solid is collected, washed with methanol, and dried to give the title compound, mp 231°-232°; NMR (CDCl3) 2.65, 4.41, 6.93, 7.14, 8.10 and 8.55 δ.

Workup

  1. filtrationthe mixture is then filtered
  2. concentrationthe tiltrate is concentrated to about 70 ml
  3. additionAdditional p-toluenesulfonic acid (0.15 g) is added
  4. temperaturethe solution is heated at 60° for 1 hr
  5. temperatureAfter cooling
  6. customthe solid is collected
  7. washwashed with methanol
  8. customdried

Sources & evidence

ORD record
ord-12b5d57484f4424fa14a3f03c110212b
Source dataset
uspto-grants-1996_11
Patent number
US05574038

Reaction notes

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