반응 #11054

ord-316141eaf6f54c0c9fa9c844294e9890

반응 방정식

CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NCc4ccccc4)c(=O)n32)cc1
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
CC=O
acetaldehyde
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
NaBH(OAc)3
CCN(CC)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2
intermediate 3a
수율 100.0%
CCN(CC)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2
(S)-[(4-{[(3-diethylamino-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 100.0%

반응 조건

상세 조건
See reaction.notes.procedure_details.

실험 절차

Following a procedure similar to that for the preparation of 1k, intermediate 1j (48 mg, 0.113 mmol), acetaldehyde (39.6 mg, 0.90 mmol) and NaBH(OAc)3 (216.2 mg, 1.02 mmol) yielded 56 mg (100%) of intermediate 3a. MS (ESI) 483.1 (M+H+).

출처

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