Benzenesulfonic acid, 3-amino-5-chloro-4-methyl- → N5-(3-chloro-2-methyl-5-sulfophenyl)-L-glutamine

Participants

Role	Name	HCID	Charge
Reactant	Benzenesulfonic acid, 3-amino-5-chloro-4-methyl-	HCID 80806	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	HOAt	HCID 181649	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	Boc-Glu-OtBu hydrochloride	HCID 131731743	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Trifluoroacetic acid	HCID 6422	—
Solvent	Acetonitrile--water (1/1)	HCID 18373917	—
Product	N5-(3-chloro-2-methyl-5-sulfophenyl)-L-glutamine	HCID 45275582	—

Reaction Steps

After 2 ml of DMF and 0.52 ml (3 mmol) of DIEA were added to 303 mg (1 mmol) of Boc-Glu-OtBu hydrochloride, 221 mg (1 mmol) of 3-amino-5-chloro-4-methylbenzenesulfonic acid, 160 mg (1.3 mmol) of HOAt and 410 mg (1.3 mmol) of HATU, the mixture was stirred at room temperature overnight. The reaction solution was diluted in water-acetonitrile and purified in accordance with the purification step A to give the protected product. The protected product obtained was dissolved in 5 ml of trifluoroacetic acid and stirred for 2 hours. After the solvent was removed by distillation, the mixture was purified in accordance with the purification step A to give the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09000208B2
Source dataset	uspto-grants-2015_04
ORD ID	ord-980e6507ccbb4b6f90bbc33ec6436beb
Source note	uspto-grants-2015_04