p-Toluenesulfonic acid monohydrate → HCID 18637511, compound

HRID 1292364Notes

Reaction equation

HRID 1292364 reaction equation
[C:1]([NH:11][C@H:12]([C:18](=[O:20])[NH2:19])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].O.[C:22]1(C)C=CC(S(O)(=O)=O)=C[CH:23]=1.CC(O)=O.[H][H].CC#N>C(O)C>[CH2:22]([O:16][C:15](=[O:17])[CH2:14][CH2:13][C@@H:12]([C:18](=[O:20])[NH2:19])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2])[CH3:23]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 6992292HCID 6992292, compoundHCID 178464491HCID 178464491, compound

Product 1

HCID 18637511HCID 18637511, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred suspension of carbobenzyloxyisoglutamine (28 g, 100 mmol) and p-toluenesulfonic acid monohydrate (1.9 g, 10 mmol) in 560 mL of absolute ethanol was gently refluxed for 12-14 hours or until TLC (1:5:94 HOAc/H2 /CH3CN) indicated that the reaction was complete.

Sources & evidence

ORD record
ord-6ae4be46fb18430da72c2488a0f399ec
Source dataset
uspto-grants-1998_05
Patent number
US05756685

Reaction notes

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