(6R,8S)-3-(allyl-benzyloxycarbonyl-amino)-8-tert-butoxycarbonylmethyl-8-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic acid → tert-butyl 2-[(6R,8S)-8-methyl-4-oxo-6-[[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]methylcarbamoyl]-3-[phenylmethoxycarbonyl(prop-2-enyl)amino]-6,7-dihydropyrrolo[1,2-a]pyrimidin-8-yl]acetate

Participants

Role	Name	HCID	Charge
Reactant	(6R,8S)-3-(allyl-benzyloxycarbonyl-amino)-8-tert-butoxycarbonylmethyl-8-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic acid	HCID 69600615	—
Reactant	N-Cbz-4-(aminomethyl)benzamidine	HCID 138391585	—
Product	tert-butyl 2-[(6R,8S)-8-methyl-4-oxo-6-[[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]methylcarbamoyl]-3-[phenylmethoxycarbonyl(prop-2-enyl)amino]-6,7-dihydropyrrolo[1,2-a]pyrimidin-8-yl]acetate	HCID 145857205	64%

Reaction Steps

Following a procedure similar to that for the preparation of 18 g, intermediate 38c (268.9 mg, 0.54 mmol) was coupled with [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester (223.9 mg, 0.70 mmol) to provide 262.3 mg (64%) of intermediate 38d. MS (ESI) 763.5 (M+H+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07094783B2
Source dataset	uspto-grants-2006_08
ORD ID	ord-c502c53106154f779abd910b4f76f1a5
Source note	uspto-grants-2006_08