(S)-2-tert-Butyl 3-methyl 7-((S)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-2,5-dihydro-1H-pyrrol-3-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate → (S)-2-tert-Butyl 3-methyl 7-((3R,5S)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)pyrrolidin-3-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate

Participants

Role	Name	HCID	Charge
Reactant	(S)-2-tert-Butyl 3-methyl 7-((S)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-2,5-dihydro-1H-pyrrol-3-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate	HCID 86705924	—
Reactant	(3S)-2-[(2S)-3,3-dimethyl-2-[[(2S)-2-(methylamino)propanoyl]amino]butanoyl]-7-[[(3S,5S)-1-[(2S)-3,3-dimethyl-2-[[(2S)-2-(methylamino)propanoyl]amino]butanoyl]-5-[[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]carbamoyl]pyrrolidin-3-yl]amino]-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-3,4-dihydro-1H-isoquinoline-3-carboxamide	HCID 117710478	—
Product	(S)-2-tert-Butyl 3-methyl 7-((3R,5S)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)pyrrolidin-3-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate	HCID 126517029	88.5%

Reaction Steps

Following a procedure analogous to that for the synthesis of Compound C of Example 20, (S)-2-tert-butyl 3-methyl 7-((5)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-2,5-dihydro-1H-pyrrol-3-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate (563 mg, 1.09 mmol) was converted to the title compound (500 mg, 88%). MS (ESI) m/z 519.5 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08889712B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-2aa2b92beac440aca82444b5dc11e4ad
Source note	uspto-grants-2014_11