p-Toluenesulfonic acid → HCID 18637511, compound

HRID 1461214Notes

Reaction equation

HRID 1461214 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:18](=[O:20])[NH2:19])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1(C)C=CC(S(O)(=O)=O)=C[CH:22]=1>C(O)C>[CH2:21]([O:16][C:15](=[O:17])[CH2:14][CH2:13][C@@H:12]([C:18](=[O:20])[NH2:19])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[CH3:22]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 6992292HCID 6992292, compound

Product 1

HCID 18637511HCID 18637511, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 15.98 g of N-Benyloxycarbonyl-L-isoglutamine in 500 mL of absolute ethanol containing 0.54 g of p-toluenesulfonic acid is refluxed for 12 hours until TLC indicated that the reaction is complete. The solution is concentrated to a small volume and addition f ether gave a solid. The solid is filtered and recrystallized to give 16.0 of N-Benyloxycarbonyl-L-isoglutamine ethyl ester, 16.

Workup

  1. temperatureis refluxed for 12 hours until TLC
  2. concentrationThe solution is concentrated to a small volume and addition f ether
  3. customgave a solid
  4. filtrationThe solid is filtered
  5. customrecrystallized

Sources & evidence

ORD record
ord-2ad4128cddd84ff488f9bffdd0eb6c9e
Source dataset
uspto-grants-1991_12
Patent number
US05075099

Reaction notes

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