Sodium hydride → HCID 66976171, 화합물

HRID 1022634노트

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HRID 1022634 반응식
[H-].[Na+].[C:3]([C:5]1[C:6]([OH:11])=[N:7][CH:8]=[CH:9][CH:10]=1)#[N:4].[Br-].[Li+].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C@@H:21]2[O:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23][C@H:22]2[CH2:35]OS(C)(=O)=O)=[CH:17][C:16]=1[F:41]>COCCOC.CN(C=O)C>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C@@H:21]2[O:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[CH2:23][C@H:22]2[CH2:35][N:7]2[CH:8]=[CH:9][CH:10]=[C:5]([C:3]#[N:4])[C:6]2=[O:11])=[CH:17][C:16]=1[F:41]

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 82050Lithium BromideHCID 86663855tert-butyl (6S,7R)-7-(4-chloro-3-fluorophenyl)-6-{[(methylsulfonyl)oxy]methyl}-1,4-oxazepane-4-carboxylateHCID 178510022HCID 178510022, 화합물

생성물 1

HCID 66976171HCID 66976171, 화합물수율 83.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 80711,2-Dimethoxyethane용매2회

실험 절차

60% Sodium hydride (0.274 g, 6.85 mmol) was added to a mixed solution of 3-cyano-2-hydroxypyridine (0.658 g, 5.48 mmol) in 1,2-dimethoxyethane (10 mL)-DMF (5 ml) under ice-cooling, and the mixture was stirred for 20 min. To the reaction solution was added lithium bromide (0.793 g, 9.13 mmol), and the mixture was stirred at room temperature for 1.5 hr. To the reaction solution was added a solution of tert-butyl (6S,7R)-7-(4-chloro-3-fluorophenyl)-6-{[(methylsulfonyl)oxy]methyl}-1,4-oxazepane-4-carboxylate (2 g, 4.57 mmol) in 1,2-dimethoxyethane (10 ml), and the mixture was stirred at 60° C. overnight. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (1.757 g, 3.80 mmol, 83%).

후처리

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 1.5 hr
  3. stirringthe mixture was stirred at 60° C. overnight
  4. concentrationThe reaction mixture was concentrated under reduced pressure, water
  5. additionwas added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-ce99abeded494467ab46034888ec7339
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722662B2

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