2-{[(Tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acid → (1r,2s)-1-{[(2s,4r)-1-[(1S)-1-((1s,2r)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid

Participants

Role	Name	HCID	Charge
Reactant	2-{[(Tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acid	HCID 5046859	—
Reactant	(1S,2R)-(-)-1-Amino-2-indanol	HCID 9866743	—
Reactant	Chlorocarbamate	HCID 22035886	—
Reactant	[1-(2-Hydroxy-indan-1-ylcarbamoyl)-2,2-dimethyl-propyl]-carbamic acid tert.butyl ester	HCID 68488177	—
Reactant	1-{[1-[1-(2-Hydroxy-indan-1-ylcarbamoyl)-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester	HCID 68491628	—
Product	(1r,2s)-1-{[(2s,4r)-1-[(1S)-1-((1s,2r)-2-hydroxy-indan-1-ylcarbamoyl)-3-phenyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid	HCID 68496226	—

Reaction Steps

N-(tert.butoxycarbonyl)-L-phenethylglycine was attached to the resin as described for the preparation of compound 16 followed by reaction with (1S,2R)-cis-1-amino-2-indanol as described for the preparation of 17 and removal of the Boc group as described for 18. The afforded compound was then reacted with the chlorocarbamate achieved from 12 as described for the preparation of 13 which gave the title compound. Purity by HPLC>95%. M+H+810.4.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07608590B2
Source dataset	uspto-grants-2009_10
ORD ID	ord-a622cef8ac2448d49cdab7316a3f2ea5
Source note	uspto-grants-2009_10