Hydrochloric Acid → HCID 57467323、化合物

HRID 1044521ノート

反応式

HRID 1044521 の反応式
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

参加物

9

反応物 5

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

生成物 1

HCID 57467323HCID 57467323、化合物

試薬・触媒・溶媒 3

HCID 3776Isopropanol溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-c3b163f1de1147d59b3bcec55b29922b
出典データセット
uspto-grants-2013_10
特許番号
US08563617B2

反応ノート

読み込み中…