Lithium Hydroxide → (+/-)-Tert-butyl (1R,5S,6S)-6-hydroxy-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate

HRID 879204노트

반응식

HRID 879204 반응식
[CH3:1][C@@H:2]1[C@H:10]2[C@H:6]([N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])C(=O)[O:9]2)[CH:5]=[C:4]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[N+:25]([O-:27])=[O:26])[CH2:3]1.[Li+].[OH-]>C1COCC1.CCOC(C)=O.C([O-])(O)=O.[Na+]>[OH:9][C@@H:10]1[C@H:6]([NH:7][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH:5]=[C:4]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[N+:25]([O-:27])=[O:26])[CH2:3][C@@H:2]1[CH3:1]

참가 물질

6

반응물 2

HCID 3939Lithium HydroxideHCID 86705252(+/-)-(3aR,7S,7aS)-tert-butyl 7-methyl-5-(3-nitropyridin-4-yl)-2-oxo-3a,6,7,7a-tetrahydrobenzo[d]oxazole-3(2H)-carboxylate

생성물 1

HCID 86705242(+/-)-Tert-butyl (1R,5S,6S)-6-hydroxy-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate수율 83%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

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온도
22 °C

실험 절차

To a solution of (+/−)-(3aR,7S,7aS)-tert-butyl 7-methyl-5-(3-nitropyridin-4-yl)-2-oxo-3a,6,7,7a-tetrahydrobenzo[d]oxazole-3(2H)-carboxylate (1.0 equiv.) in THF (0.20 M) was added 2M LiOH (3.0 equiv.) was added. The mixture was stirred overnight 20 hrs at 22° C. The mixture was diluted with EtOAc and NaHCO3(aq.). The layers were separated and the aqueous was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated. The golden foam was purified by ISCO chromatography to afford (+/−)-tert-butyl ((1R,5S,6S)-6-hydroxy-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-en-1-yl)carbamate in 83% yield. LC/MS (m/z)=350.2 (MH+), Rt=0.82 min.

후처리

  1. additionwas added
  2. customThe layers were separated
  3. extractionthe aqueous was extracted with EtOAc
  4. washThe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe golden foam was purified by ISCO chromatography

출처 및 근거

ORD 기록
ord-ed732b141e714177bb3493f055ae31cf
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987457B2

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