Sodium Azide → (+/-)-tert-butyl ((1R,2R,3 S,5R)-5-(3-aminopyridin-4-yl)-2-azido-3-methyl cyclohexyl)carbamate

HRID 879195노트

반응식

HRID 879195 반응식
CS(O[C@H:6]1[C@@H:11]([CH3:12])[CH2:10][C@@H:9]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[NH2:19])[CH2:8][C@H:7]1[NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])(=O)=O.[N-:28]=[N+:29]=[N-:30].[Na+]>CN(C=O)C>[NH2:19][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:13]=1[C@H:9]1[CH2:8][C@@H:7]([NH:20][C:21](=[O:22])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C@H:6]([N:28]=[N+:29]=[N-:30])[C@@H:11]([CH3:12])[CH2:10]1

참가 물질

4

반응물 2

HCID 33557Sodium AzideHCID 86705243(+/-)-(1S,2R,4R,6S)-4-(3-aminopyridin-4-yl)-2-((tert-butoxycarbonyl)amino)-6-methylcyclohexyl methanesulfonate

생성물 1

HCID 86705244(+/-)-tert-butyl ((1R,2R,3 S,5R)-5-(3-aminopyridin-4-yl)-2-azido-3-methyl cyclohexyl)carbamate수율 87%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (+/−)-(1S,2R,4R,6S)-4-(3-aminopyridin-4-yl)-2-((tert-butoxycarbonyl)amino)-6-methylcyclohexyl methanesulfonate (1.0 equiv.) in DMF (0.20 M) was added NaN3 (7.0 equiv.). The solution was submerged in a 70° C. oil bath and left stirring under Ar for 4 hrs. The solution was cooled to rt and left stirring under Ar overnight. The solution was partitioned between EtOAc and H2O. The organic layer was washed with Na2CO3(sat.), NaCl(sat.), dried over MgSO4, filtered, concentrated to yield (+/−)-tert-butyl ((1R,2R,3S,5R)-5-(3-aminopyridin-4-yl)-2-azido-3-methyl cyclohexyl)carbamate in 87% yield. LC/MS (m/z)=347.3 (MH+), Rt=0.68 min.

후처리

  1. customwas submerged in a 70° C.
  2. waitleft
  3. waitleft
  4. stirringstirring under Ar overnight
  5. customThe solution was partitioned between EtOAc and H2O
  6. washThe organic layer was washed with Na2CO3(sat.), NaCl(sat.)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-920974099c6d4a5199a5170ea4f290f9
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987457B2

반응 노트

불러오는 중…