(S)-8,8-diallyl-3-(allyl-benzyloxycarbonyl-amino)-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic Acid → benzyl N-[(6S)-4-oxo-6-[[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]methylcarbamoyl]-8,8-bis(prop-2-enyl)-6,7-dihydropyrrolo[1,2-a]pyrimidin-3-yl]-N-prop-2-enylcarbamate

Participants

Role	Name	HCID	Charge
Reactant	(S)-8,8-diallyl-3-(allyl-benzyloxycarbonyl-amino)-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic Acid	HCID 57444829	—
Reactant	Benzyl ((4-(aminomethyl)phenyl)(imino)methyl)carbamate hydrochloride	HCID 145832047	—
Reactant	benzyl N-[(6S,8R)-4-oxo-6-[[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]methylcarbamoyl]-8-prop-2-enyl-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidin-3-yl]-N-prop-2-enylcarbamate	HCID 145857219	—
Product	benzyl N-[(6S)-4-oxo-6-[[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]methylcarbamoyl]-8,8-bis(prop-2-enyl)-6,7-dihydropyrrolo[1,2-a]pyrimidin-3-yl]-N-prop-2-enylcarbamate	HCID 145857218	41%

Reaction Steps

According to the procedure for the preparation of 28e, 29d (162 mg, 0.360 mmol) was coupled with [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester hydrochloride to afford after flash chromatography (66% EtOAc/hexanes) 105 mg (41%) of 29e. MS (ESI) 715.5 (M+H+), 737.5 (M+Na+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07094783B2
Source dataset	uspto-grants-2006_08
ORD ID	ord-4f9a90965b4c40a7adc1535c3ce407ad
Source note	uspto-grants-2006_08