Diisopropylcarbodiimide → N-(3-{1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}-benzyl)-2-[2-({2-[2-(3,4,5,6,7-pentahydroxy-2-oxoheptyloxy)ethoxy]ethylcarbamoyl}-methoxy)ethoxy]acetamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylcarbodiimide	HCID 12734	—
Reactant	4-(3-Aminomethylphenyl)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one	HCID 22252037	—
Reactant	[2-({2-[2-(3,4,5,6,7-Pentahydroxy-2-oxoheptyloxy)ethoxy]ethylcarbamoyl}methoxy)ethoxy]acetic acid	HCID 22252049	—
Reactant	HCID 178418300	HCID 178418300	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-(3-{1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}-benzyl)-2-[2-({2-[2-(3,4,5,6,7-pentahydroxy-2-oxoheptyloxy)ethoxy]ethylcarbamoyl}-methoxy)ethoxy]acetamide	HCID 22252072	—

Reaction Steps

31 is prepared similarly to 18 starting from 68 mg of 4-(3-aminomethylphenyl)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one (15), 76 mg of [2-({2-[2-(3,4,5,6,7-pentahydroxy-2-oxoheptyloxy)ethoxy]ethylcarbamoyl}methoxy)-ethoxy]acetic acid (27), 62 μl of diisopropylcarbodiimide and 44 mg of hydroxybenzotriazole in 2 ml of dimethylformamide. This gives 31: C43H55F2N3O14 (875.93) MS (ESI) 876 (M+H)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07576200B2
Source dataset	uspto-grants-2009_08
ORD ID	ord-074f077ddbba42059188845b3139a660
Source note	uspto-grants-2009_08