Reaktion #11089

ord-4f9a90965b4c40a7adc1535c3ce407ad

Reaktionsgleichung

[(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester hydrochloride

C=CC[C@@H]1C[C@@H](C(=O)NCc2ccc(C(=N)NC(=O)OCc3ccccc3)cc2)n2c1ncc(N(CC=C)C(=O)OCc1ccccc1)c2=O

28e

benzyl (6S,8R)-allyl-{8-allyl-6-[4-(benzyloxycarbonylamino-imino-methyl)-benzylcarbamoyl]-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-carbamate

C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)O)CC2(CC=C)CC=C

29d

(S)-8,8-diallyl-3-(allyl-benzyloxycarbonyl-amino)-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic acid

→

C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)CC2(CC=C)CC=C

29e

Ausbeute 41.0%

benzyl (S)-allyl-{8,8-diallyl-6-[4-(benzyloxycarbonylamino-imino-methyl)-benzylcarbamoyl]-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-carbamate

Ausbeute 41.0%

Edukte

[(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester hydrochloride

28e

benzyl (6S,8R)-allyl-{8-allyl-6-[4-(benzyloxycarbonylamino-imino-methyl)-benzylcarbamoyl]-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-carbamate

29d

(S)-8,8-diallyl-3-(allyl-benzyloxycarbonyl-amino)-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic acid

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen

See reaction.notes.procedure_details.

Vorschrift

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+).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07094783B2uspto-grants-2006_08