Reacción #11085

ord-6ece1c29cc1b4b1eab7b6792a465b241

Ecuación de reacción

CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1
intermediate 1k
CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1
(6S)-[(4-{[(3-benzylamino-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carbonyl)-amino]-methyl}-phenyl)-imino-methyl]-carbamic acid tert-butyl ester
C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)N
26a
C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)N
(6S,8R)-alIyl-{8-amino-6-[4-(benzyloxycarbonylamino-imino-methyl)-benzylcarbamoyl]-8-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo [1,2-a]pyrimidin-3-yl}-carbamic acid benzyl ester
CC(C)=O
acetone
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
NaBH(OAc)3
→
C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)NC(C)C
27a
Rendimiento 28.1%
C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)NC(C)C
(6S,8R)-allyl-{6-[4-(benzyloxycarbonylamino-imino-methyl)-benzylcarbamoyl]-8-isopropylamino-8-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl}-carbamic acid benzyl ester
Rendimiento 28.1%

Reactantes

CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1
intermediate 1k
CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1
(6S)-[(4-{[(3-benzylamino-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carbonyl)-amino]-methyl}-phenyl)-imino-methyl]-carbamic acid tert-butyl ester
C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)N
26a
C=CCN(C(=O)OCc1ccccc1)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OCc3ccccc3)cc1)C[C@@]2(C)N
(6S,8R)-alIyl-{8-amino-6-[4-(benzyloxycarbonylamino-imino-methyl)-benzylcarbamoyl]-8-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo [1,2-a]pyrimidin-3-yl}-carbamic acid benzyl ester
CC(C)=O
acetone
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
NaBH(OAc)3

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Procedimiento

Following a procedure similar to that for the preparation of intermediate 1k, 26a (30 mg, 0.045 mmol), acetone (5.3 mg, 0.090 mmol) and NaBH(OAc)3 (26.8 mg, 0.127 mmol) yielded 8.9 mg (28.1%) of 27a. MS (ESI) 706.2 (M+H+).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07094783B2uspto-grants-2006_08