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Water → tert-Butyl 3-fluoro-4-oxoazepane-1-carboxylate

HRID 876418
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HRID 876418 반응식
[F:1][CH:2]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][CH2:5][CH:4](C(OCC)=O)[C:3]1=[O:21].O.[Li+].[Cl-]>CS(C)=O>[F:1][CH:2]1[C:3](=[O:21])[CH2:4][CH2:5][CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8]1
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참가 물질

5

반응물 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 67230662644982-11-6

생성물 1

HCID 53415294tert-Butyl 3-fluoro-4-oxoazepane-1-carboxylate수율 21%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
125 °C

실험 절차

The product from Step A was dissolved in DMSO (200 mL) and H2O (8.29 g, 460 mmol) followed by addition of LiCl (19.5 g, 460 mmol). The solution was warmed to 125° C. and the mixture was stirred overnight. The mixture was cooled to ambient temperature and partitioned between EtOAc (2.5 L) and water:brine (1:1, 2.0 L). The mixture was filtered through activated charcoal over Celite, which was washed with EtOAc, forming visible layers. The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (10 to 80% EtOAc/hexanes) providing 4.5 g (21%) of the product as a thick pale orange oil.

후처리

  1. temperatureThe mixture was cooled to ambient temperature
  2. custompartitioned between EtOAc (2.5 L) and water:brine (1:1, 2.0 L)
  3. filtrationThe mixture was filtered through activated charcoal over Celite, which
  4. washwas washed with EtOAc
  5. customforming visible layers
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (10 to 80% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-f927669aee73420db3c90821f3d43d22
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08987251B2

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