반응 #11057

ord-77ff826270494a869c96dd5332baae40

반응 방정식

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
CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1
intermediate 1j
CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(N)c(=O)n32)cc1
(S)-[(4-{[(3-amino-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carbonyl)-amino]-methyl}-phenyl)-imino-methyl]-carbamic acid tert-butyl ester
O=C1CCCC1
cyclopentanone
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
NaBH(OAc)3
CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NC4CCCC4)c(=O)n32)cc1
intermediate 6a
수율 57.3%
CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NC4CCCC4)c(=O)n32)cc1
(S)-[(4-{[(3-cyclopentylamino-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carbonyl)-amino]-methyl}-phenyl)-imino-methyl]-carbamic acid tert-butyl ester
수율 57.3%

반응 조건

상세 조건
See reaction.notes.procedure_details.

실험 절차

Following a procedure similar to that for the preparation of intermediate 1k, intermediate 1j (115.2 mg, 0.27 mmol), cyclopentanone (68.1 mg, 0.81 mmol) and NaBH(OAc)3 (217.5 mg, 1.03 mmol) yielded 76.5 mg (57.3%) of intermediate 6a. MS (ESI) 496.1 (M+H+).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07094783B2uspto-grants-2006_08