3-Aminobenzenesulfonic acid → 3-[(4S)-4-amino-5-methoxy-5-oxopentanamido]benzene-1-sulfonic acid

Participants

Role	Name	HCID	Charge
Reactant	3-Aminobenzenesulfonic acid	HCID 8474	—
Reactant	HOAt	HCID 181649	—
Reactant	(4S)-4-(((tert-butoxy)carbonyl)amino)-5-methoxy-5-oxopentanoic acid	HCID 7018754	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Trifluoroacetic acid	HCID 6422	—
Solvent	Triethylamine	HCID 8471	—
Product	3-[(4S)-4-amino-5-methoxy-5-oxopentanamido]benzene-1-sulfonic acid	HCID 53379292	—

Reaction Steps

Boc-Glu-OME, 130 mg (0.5 mmol), 190 mg (0.5 mmol) of 2-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU), 70 mg (0.5 mmol) of 7-aza-1-hydroxybenzotriazole (HOAt) and 87 mg (0.5 mmol) of 3-aminobenzenesulfonic acid were suspended in 2.0 ml of methylene chloride, and 0.5 ml of triethylamine was added to the suspension. The mixture was stirred at room temperature overnight. After the solvent was removed by distillation, the purification step A was applied to give the intermediate. The crude product was dissolved in 4.0 ml of trifluoroacetic acid (TFA) and stirred at room temperature for an hour. After the solvent was removed by distillation, the purification step A was applied to give 7.4 mg of the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08877739B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-db182332e4ce4210a912e5dd18932d79
Source note	uspto-grants-2014_11