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Sodium Bicarbonate → racemic tert-butyl ((5RS,6RS)-5-(2-fluoro-5-nitrophenyl)-6-(2-hydroxyethyl)-2,2,5-trimethyl-1,1-dioxido-5,6-dihydro-2H-1,4-thiazin-3-yl)carbamate

HRID 627597
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HRID 627597 반응식
[CH2:1]([CH:4]1[S:9](=[O:11])(=[O:10])[C:8]([CH3:13])([CH3:12])[C:7]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[N:6][C:5]1([C:23]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[CH:25][C:24]=1[F:32])[CH3:22])[CH:2]=C.C(=O)(O)[O-:34].[Na+].[BH4-].[Na+]>C(Cl)Cl.CO>[F:32][C:24]1[CH:25]=[CH:26][C:27]([N+:29]([O-:31])=[O:30])=[CH:28][C:23]=1[C:5]1([CH3:22])[CH:4]([CH2:1][CH2:2][OH:34])[S:9](=[O:11])(=[O:10])[C:8]([CH3:13])([CH3:12])[C:7]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[N:6]1
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참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86728096tert-butyl ((5RS,6SR)-6-allyl-5-(2-fluoro-5-nitrophenyl)-2,2,5-trimethyl-1,1-dioxido-5,6-dihydro-2H-1,4-thiazin-3-yl)carbamate

생성물 1

HCID 131735324racemic tert-butyl ((5RS,6RS)-5-(2-fluoro-5-nitrophenyl)-6-(2-hydroxyethyl)-2,2,5-trimethyl-1,1-dioxido-5,6-dihydro-2H-1,4-thiazin-3-yl)carbamate수율 99%

시약·촉매·용매 2

HCID 887Methanol용매
HCID 6344Dichloromethane용매

실험 절차

A solution of tert-butyl ((5RS,6RS)-6-allyl-5-(2-fluoro-5-nitrophenyl)-2,2,5-trimethyl-1,1-dioxido-5,6-dihydro-2H-1,4-thiazin-3-yl)carbamate (120 mg, 0.256 mmol) in DCM (1.8 ml) and MeOH (0.6 ml) was cooled to −78° C., and sodium bicarbonate (42.9 mg, 0.511 mmol) was added and the mixture was ozonolyzed for 10 min. Oxygen was bubbled through the solution for 2 min, then solid sodium borohydride (14.5 mg, 0.383 mmol) was added to the mixture and the mixture was removed from the cooling bath and was allowed to reach RT and stirred for 30 min. The reaction was quenched with sat. solution of NH4Cl and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated to afford crude racemic tert-butyl ((5RS,6RS)-5-(2-fluoro-5-nitrophenyl)-6-(2-hydroxyethyl)-2,2,5-trimethyl-1,1-dioxido-5,6-dihydro-2H-1,4-thiazin-3-yl)carbamate (120 mg, 0.253 mmol, 99% yield) which was used without further purification.

후처리

  1. customOxygen was bubbled through the solution for 2 min
  2. customthe mixture was removed from the cooling bath
  3. customto reach RT
  4. customThe reaction was quenched with sat. solution of NH4Cl
  5. extractionextracted with EtOAc
  6. washThe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-66ef482e419a40d4a03e8226011ce94e
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09309263B2

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