5-Bromo-N-((1SR,2RS)-2-hydroxy-cyclohexyl)-6-(2,2,2-trifluoro-ethoxy)-nicotinamide → 5-Bromo-N-((1S,2R)-2-hydroxy-cyclohexyl)-6-(2,2,2-trifluoro-ethoxy)-nicotinamide

HRID 1516382

반응식

HRID 1516382 반응식
[Br:1][C:2]1[C:3]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[N:4][CH:5]=[C:6]([CH:17]=1)[C:7]([NH:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[OH:16])=[O:8]>CCCCCCC.C(O)(C)C>[Br:1][C:2]1[C:3]([O:18][CH2:19][C:20]([F:22])([F:23])[F:21])=[N:4][CH:5]=[C:6]([CH:17]=1)[C:7]([NH:9][C@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[OH:16])=[O:8]

참가 물질

3

반응물 1

HCID 581925915-Bromo-N-((1SR,2RS)-2-hydroxy-cyclohexyl)-6-(2,2,2-trifluoro-ethoxy)-nicotinamide

생성물 1

HCID 698122955-Bromo-N-((1S,2R)-2-hydroxy-cyclohexyl)-6-(2,2,2-trifluoro-ethoxy)-nicotinamide수율 47.7%

시약·촉매·용매 1

HCID 21225753Isopropanol heptane용매

실험 절차

5-Bromo-N-((1SR,2RS)-2-hydroxy-cyclohexyl)-6-(2,2,2-trifluoro-ethoxy)-nicotinamide (91.3 g, 0.23 mol) was submitted to preparative HPLC on ChiralPak AD® (250×110 mm column) using n-heptane/isopropanol 85/15 as mobile phase. Baseline separation was achieved and the title compound (43.6 g) was isolated as colorless solid from the first peak; MS (ISP) 395.2, 397.2 (M−H); ORD (589 nM, 20° C., CHCl3) −21.6°.

후처리

  1. customBaseline separation

출처 및 근거

ORD 기록
ord-ace58693f81548459d536001f485cad8
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227491B2

연결된 노트

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