(+/-)-tert-butyl (1R,5S,6S)-5-methyl-6-(2-(methylsulfonyl)ethoxy)-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate → tert-butyl ((1R,2S,3S,5R)-5-(3-aminopyridin-4-yl)-3-methyl-2-(2-(methylsulfonyl)ethoxy)cyclohexyl)carbamate

HRID 705298노트

반응식

HRID 705298 반응식
[CH3:1][C@@H:2]1[C@H:7]([O:8][CH2:9][CH2:10][S:11]([CH3:14])(=[O:13])=[O:12])[C@H:6]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:5]=[C:4]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][C:24]=2[N+:29]([O-])=O)[CH2:3]1>CCO.[Pd]>[NH2:29][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][C:23]=1[C@H:4]1[CH2:5][C@@H:6]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C@@H:7]([O:8][CH2:9][CH2:10][S:11]([CH3:14])(=[O:13])=[O:12])[C@@H:2]([CH3:1])[CH2:3]1

참가 물질

4

반응물 1

HCID 86705262(+/-)-tert-butyl (1R,5S,6S)-5-methyl-6-(2-(methylsulfonyl)ethoxy)-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate

생성물 1

HCID 86705263tert-butyl ((1R,2S,3S,5R)-5-(3-aminopyridin-4-yl)-3-methyl-2-(2-(methylsulfonyl)ethoxy)cyclohexyl)carbamate수율 55%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

To a solution of (+/−)-tert-butyl (1R,5S,6S)-5-methyl-6-(2-(methylsulfonyl)ethoxy)-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate (1.0 equiv.) in degassed EtOH (0.17 M) was added Pd/C (0.3 equiv.). The mixture was purged with H2, and allowed to stir under H2 overnight at RT. The reaction was filtered through a pad of celite and the cake was washed with MeOH. The organics were concentrated and purified by ISCO SiO2 chromatography to yield (+/−)-tert-butyl (1R,2S,3S,5R)-5-(3-aminopyridin-4-yl)-3-methyl-2-(2-(methylsulfonyl)ethoxy)cyclohexylcarbamate in 55% yield. LC/MS (m/z)=428.2 (MH+), Rt=0.59 min. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.07 (d, J=6.85 Hz, 3 H), 1.46 (s, 9 H), 1.72-1.88 (m, 2 H), 2.62 (tt, J=12.23, 3.30 Hz, 1 H), 3.08 (s, 3 H), 3.21 (d, J=14.62 Hz, 1 H), 3.35-3.47 (m, 1 H), 3.58 (br. s., 1 H), 3.64 (br. s., 2 H), 3.70-3.86 (m, 1 H), 3.94-4.10 (m, 1 H), 4.10-4.22 (m, 1 H), 5.43 (d, J=9.00 Hz, 1 H), 6.89 (d, J=5.04 Hz, 1 H), 7.98 (d, J=4.99 Hz, 1 H), 8.03 (s, 1 H).

후처리

  1. customThe mixture was purged with H2
  2. filtrationThe reaction was filtered through a pad of celite
  3. washthe cake was washed with MeOH
  4. concentrationThe organics were concentrated
  5. custompurified by ISCO SiO2 chromatography

출처 및 근거

ORD 기록
ord-25c6205d2db94d63b1098be2ab290238
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09173883B2

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