2-Naphthalenesulfonyl chloride → HCID 178427607, compound

Participants

Role	Name	HCID	Charge
Reactant	2-Naphthalenesulfonyl chloride	HCID 7125	—
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	4-[(S)-2-Amino-5-({amino-[(E)-2,2,4,6,7-pentamethyl-2,3-dihydro-benzofuran-5-sulfonylimino]-methyl)-amino)-pentanoyl]-piperazine-1-carboxylic acid tert-butyl ester	HCID 178427562	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 178427607	HCID 178427607	100%

Reaction Conditions

Temperature	5 °C

Reaction Steps

To a solution of compound B (28.0 g, 46.2 mmol) in THF (250 mL) was added aqueous 1N NaOH (171 mL). The reaction mixture was cooled to ˜5° C., a solution of 2-naphthalene sulfonylchloride (26.19 g, 115.6 mmol) in THF (125 mL) was added dropwise. The reaction mixture was stirred at ˜5° C. for 10 min, with stirring continued at room temperature for 2 h. The reaction mixture was diluted with EtOAc (1 L), washed with aqueous 1N NaOH (1 L), water (1 L) and brine (1 L). The organic layer was separated, dried over Na2SO4 and removal of the solvent in vacuo to afford compound C (36.6 g, 46.2 mmol). LC-MS [M+H] 785.5 (C38H52N6O8S2+H, calc: 785.9).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09040032B2
Source dataset	uspto-grants-2015_05
ORD ID	ord-9e8b7014068f4ba88babcf4775f6c13e
Source note	uspto-grants-2015_05