Methanesulfonyl chloride → HCID 67412114, compound

https://huagongshe.com/reaction/1949641

Participants

Role	Name	HCID	Charge
Reactant	Methanesulfonyl chloride	HCID 31297	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid methyl ester	HCID 67409757	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 67412114	HCID 67412114	49.4%

Reaction Conditions

Temperature	0 °C

Reaction Steps

A solution containing 50 (200 mg, 0.41 mmol) and DIPEA (163 mg, 1.26 mmol) in anhydrous DCM (5 mL) was cooled to 0° C. A solution of MsCl (44 mg, 0.41 mmol) in DCM (0.5 mL) was added followed by the addition of DMAP (5 mg, cat.). After 2 h, the reaction mixture was diluted with DCM and washed successively with 1M HCl and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by flash silica gel chromatography (1:1 hexanes/EtOAc) to afford 114 mg (49%) of 61 as a white solid. Mass spectrum, m/z [563] (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08399683B2
Source dataset	uspto-grants-2013_03
ORD ID	ord-5c5f7ea2c620410da85a3707a53e7648
Source note	uspto-grants-2013_03