Toluene → HCID 86762221, 화합물

HRID 338132

반응식

HRID 338132 반응식
[C:1]([NH:9][C:10]1[S:11][CH2:12][C@@H:13]2[CH2:18][N:17]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH2:16][C@:14]2([C:29]2[S:30][C:31](Br)=[CH:32][CH:33]=2)[N:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:35]([N:39]1C=CN=C1)CCC.C1(C)C=CC=CC=1>C(OCC)(=O)C.O.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[K+].[K+].[K+].[K+].[Fe+6].[Cu]I>[C:1]([NH:9][C:10]1[S:11][CH2:12][C@@H:13]2[CH2:18][N:17]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH2:16][C@:14]2([C:29]2[S:30][C:31]([C:35]#[N:39])=[CH:32][CH:33]=2)[N:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 3

HCID 1140TolueneHCID 61347ButylimidazoleHCID 86762219HCID 86762219, 화합물

생성물 1

HCID 86762221HCID 86762221, 화합물수율 74%

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 11963580Ferrate(4-), hexakis(cyano-C)-, tetrapotassium, (OC-6-11)-촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
145 °C

실험 절차

Benzyl (4aR,7aR)-2-(benzoylamino)-7a-(5-bromothiophen-2-yl)-4a,5,7,7a-tetrahydropyrrolo[3,4-d][1,3]thiazine-6(4H)-carboxylate (3.88 g, 6.97 mmol), anhydrous potassium hexacyanoferrate (II) (2.57 g, 6.97 mmol) (prepared as cited in Schareina, T.; et al Synthesis, 2008, 20, 3351-3355), copper (I) iodide (398 mg, 2.09 mmol), 1-butylimidazole (2.8 mL, 20.9 mmol), and toluene (23 mL) are added to a 60 mL glass pressure tube fitted with a stirrer bar. A stream of nitrogen is passed over the mixture for a few minutes and the pressure tube is then sealed. The stirred mixture is heated at 145° C. for 18 hours. The resulting dark mixture is cooled to room temperature. The mixture is diluted with ethyl acetate (100 mL) and water (15 mL) and vacuum filtered through a pad of diatomaceous earth while rinsing with ethyl acetate (100 mL) and water (15 mL). The layers of the filtrate are separated and the organic layer is further washed with water (2×30 mL) and brine (30 mL). The organic phase is dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica gel flash chromatography eluting with a hexanes/ethyl acetate, gradient from 80:20 to 0:100, to give the title compound (2.59 g, 74%) as a white foam: ES/MS (m/z): 503.2 (M+H).

후처리

  1. customfitted with a stirrer bar
  2. waitA stream of nitrogen is passed over the mixture for a few minutes
  3. customthe pressure tube is then sealed
  4. temperatureThe resulting dark mixture is cooled to room temperature
  5. filtrationfiltered through a pad of diatomaceous earth
  6. washwhile rinsing with ethyl acetate (100 mL) and water (15 mL)
  7. customThe layers of the filtrate are separated
  8. washthe organic layer is further washed with water (2×30 mL) and brine (30 mL)
  9. dry with materialThe organic phase is dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe residue is purified by silica gel flash chromatography
  13. washeluting with a hexanes/ethyl acetate, gradient from 80:20 to 0:100

출처 및 근거

ORD 기록
ord-b4764b344aac40128a11ce0aaf2b7c0f
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889856B2

연결된 노트

불러오는 중…