1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 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

関与物質

役割	名称	HCID	仕込み量
反応物	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
反応物	HOAt	HCID 181649	—
反応物	Sodium Bicarbonate	HCID 516892	—
反応物	(6S,8R)-8-allyl-3-(allyl-benzyloxycarbonyl-amino)-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic Acid	HCID 57444828	—
反応物	Benzyl ((4-(aminomethyl)phenyl)(imino)methyl)carbamate hydrochloride	HCID 145832047	—
溶媒	Ethyl Acetate	HCID 8857	—
溶媒	dichloromethane N,N-dimethylformamide	HCID 22350042	—
生成物	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	20.8%

反応手順

To a solution of 28d (172 mg, 0.420 mmol) and [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester hydrochloride (180 mg, 0.504 mmol) in 3.6 mL CH2Cl2/DMF (5:1) at 0° C., was added HOAT (113 mg, 0.588 mmol), NaHCO3 (141 mg, 1.68 mmol), and EDCI (113 mg, 0.588 mmol). The mixture was allowed to warm to rt and stir for 64 h. The reaction was diluted with EtOAc and the organic phase was washed with H2O, 1N HCl, H2O, and brine. The organic phase was dried (Na2SO4) and concentrated. The residue obtained was purified by flash chromatography (75% EtOAc/hexanes) to afford 59 mg of intermediate 28e.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US07094783B2
出典データセット	uspto-grants-2006_08
ORD ID	ord-384eab5d229c455fb8dd63aeadcf8621
出典メモ	uspto-grants-2006_08