Réaction #11100

ord-c502c53106154f779abd910b4f76f1a5

Équation de réaction

C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)O)C[C@@]2(C)CC(=O)OC(C)(C)C
intermediate 38c
C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)O)C[C@@]2(C)CC(=O)OC(C)(C)C
(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
N=C(NC(=O)OCc1ccccc1)c1ccc(CN)cc1
[(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester
→
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)OC(C)(C)C
intermediate 38d
Rendement 64.0%
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)OC(C)(C)C
(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 tert-butyl ester
Rendement 64.0%

Réactifs

C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)O)C[C@@]2(C)CC(=O)OC(C)(C)C
intermediate 38c
C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@@H](C(=O)O)C[C@@]2(C)CC(=O)OC(C)(C)C
(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
N=C(NC(=O)OCc1ccccc1)c1ccc(CN)cc1
[(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester

Réactifs

Aucun

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

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+).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07094783B2uspto-grants-2006_08