Trifluoroacetic acid → tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-{[(1S,2R)-1-(1,2-oxazinan-2-ylcarbonyl)-2-phenylcyclopropyl]amino)-3-oxopropyl]pyrrolidine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Trifluoroacetic acid	HCID 6422	—
Reactant	(1S,2R)-N-Boc-1-amino-2-phenylcyclopropanecarboxylic acid	HCID 7009512	—
Reactant	(3R,4S,5S)-tert-butyl 4-((S)-2-(((benzyloxy)carbonyl)amino)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoate	HCID 10529182	—
Reactant	tert-Butyl[(2S)-1-(1,2-oxazinan-2-yl)-1-oxo-3-phenylpropan-2-yl]carbamate	HCID 89181604	—
Product	tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-{[(1S,2R)-1-(1,2-oxazinan-2-ylcarbonyl)-2-phenylcyclopropyl]amino)-3-oxopropyl]pyrrolidine-1-carboxylate	HCID 86678340	—

Reaction Steps

The title compound was prepared analogously to the synthesis of Intermediates 5 and 6 in three steps by coupling commercially available (1S,2R)-1-[(tert-butoxycarbonyl)amino]-2-phenylcyclopropanecarboxylic acid with 1,2-oxazinane hydrochloride (Starting Material 5), subsequent deprotection with trifluoroacetic acid and another coupling with Starting Material 1. The end product was purified by preparative HPLC.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08722629B2
Source dataset	uspto-grants-2014_05
ORD ID	ord-d526ba0a9af74003bc4599b3c4675786
Source note	uspto-grants-2014_05