Reaktion #11103

ord-dab4932fb5d1424e8f1c73ce5b065778

Reaktionsgleichung

C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)O
intermediate 39a
C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)O
(6R,8S)-{3-(allyl-benzyloxycarbonyl-amino)-6-[4-(benzyloxycarbonylamino-imino-methyl)-benzylcarbamoyl]-8-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-8-yl}-acetic acid
C1CCNCC1
piperidine
→
C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)N1CCCCC1
intermediate 41a
Ausbeute 72.5%
C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)N1CCCCC1
(6R,8S)-allyl-[6-[4-(benzyloxycarbonylamino-imino-methyl)-benzylcarbamoyl]-8-methyl-4-oxo-8-(2-oxo-2-piperidin-1-yl-ethyl)-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl]-carbamic acid benzyl ester
Ausbeute 72.5%

Edukte

—
intermediate
C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)O
intermediate 39a
C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)CC(=O)O
(6R,8S)-{3-(allyl-benzyloxycarbonyl-amino)-6-[4-(benzyloxycarbonylamino-imino-methyl)-benzylcarbamoyl]-8-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-8-yl}-acetic acid
C1CCNCC1
piperidine

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Following a procedure similar to that for the preparation of intermediate 18 g, intermediate 39a (20 mg, 0.028 mmol) was coupled with piperidine (8.1 mg, 0.14 mmol) to provide 15.7 mg (71%) of intermediate 41a. MS (ESI) 774.5 (M+H+).

Quelle

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