Hydrochloric Acid → HCID 57467323, 화합물

HRID 2177105노트

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HRID 2177105 반응식
FC1C=C(C=CC=1)CC1C2C(=CC=C(CCCNS(CCC)(=O)=O)C=2)CCC1NC(=O)[O-].CI.C(=O)([O-])[O-].[Cs+].[Cs+].[F:41][C:42]1[CH:43]=[C:44]([CH:75]=[CH:76][CH:77]=1)[CH2:45][CH:46]1[C:55]2[C:50](=[CH:51][CH:52]=[C:53]([CH2:56][CH2:57][CH2:58][N:59]([CH3:66])[S:60]([CH2:63][CH2:64][CH3:65])(=[O:62])=[O:61])[CH:54]=2)[CH2:49][CH2:48][CH:47]1[NH:67]C(=O)OC(C)(C)C.[ClH:78]>C(#N)C.C(OCC)(=O)C.C(O)(C)C>[ClH:78].[NH2:67][CH:47]1[CH:46]([CH2:45][C:44]2[CH:75]=[CH:76][CH:77]=[C:42]([F:41])[CH:43]=2)[C:55]2[CH:54]=[C:53]([CH2:56][CH2:57][CH2:58][N:59]([CH3:66])[S:60]([CH2:63][CH2:64][CH3:65])(=[O:62])=[O:61])[CH:52]=[CH:51][C:50]=2[CH2:49][CH2:48]1

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 57467325HCID 57467325, 화합물HCID 68513853tert-butyl 1-(3-fluorobenzyl)-7-(3-(N-methylpropylsulfonamido)propyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate

생성물 1

HCID 57467323HCID 57467323, 화합물

시약·촉매·용매 3

HCID 3776Isopropanol용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

tert-Butyl (1-(3-fluorobenzyl)-7-(3-(propylsulfonamido)propyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (cf. 209 and 201a, 65 mg, 0.125 mmol) was dissolved in acetonitrile (800 μL) and methyl iodide (24 μL, 0.376 mmol) and cesium carbonate (0.102 g, 0.313 mmol) was added. The reaction mixture was heated for 24 hours in a sealed vessel to 80° C. The reaction mixture was diluted with ethyl acetate. The ethyl acetate solution was successively washed with water and saturated sodium chloride solution. The organic phase was dried (MgSO4) and concentrated in vacuo. The crude product was purified by preparative thin-layer chromatography (silica gel, dichloromethane, methanol). The obtained tert-butyl 1-(3-fluorobenzyl)-7-(3-(N-methylpropylsulfonamido)propyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (65 mg, 0.122 mmol) was dissolved in 4 M hydrochloric acid in isopropanol and stirred at room temperature for 4 hours. The solvent was removed in vacuo. Diethyl ether was added and the precipitate removed by filtration and dried. Yield: 22 mg (0.047 mmol, 38%).

후처리

  1. washThe ethyl acetate solution was successively washed with water and saturated sodium chloride solution
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by preparative thin-layer chromatography (silica gel, dichloromethane, methanol)
  5. customThe solvent was removed in vacuo
  6. additionDiethyl ether was added
  7. customthe precipitate removed by filtration
  8. customdried

출처 및 근거

ORD 기록
ord-fc3f3b93541a410f907812dc4b1b92f5
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067871B2

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