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Triethylamine → benzyl (NE)-N-[[1-[1-(4-fluorophenyl)cyclobutyl]-7-[2-(propylsulfonylamino)ethoxy]-3,4-dihydro-1H-isoquinolin-2-yl]-(phenylmethoxycarbonylamino)methylidene]carbamate

HRID 242073
ノート
印刷プレビュー

反応式

HRID 242073 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])[CH:20]=4)[CH2:15][CH2:14][NH:13]3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CS[C:34]([NH:46][C:47](=[O:56])[O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[N:35][C:36](=[O:45])[O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(N(CC)CC)C>CN(C)C=O.FC(F)(F)S([O-])(=O)=O.[Ag+]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:27])=[O:28])[CH:20]=4)[CH2:15][CH2:14][N:13]3/[C:34](/[NH:46][C:47](=[O:56])[O:48][CH2:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[N:35]/[C:36](=[O:45])[O:37][CH2:38][C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH2:9][CH2:10][CH2:11]2)=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 46642131,3-Bis(benzyloxycarbonyl)-2-methylisothioureaHCID 66868509N-[2-({1-[1-(4-Fluorophenyl)cyclobutyl]-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)ethyl]propane-1-sulfonamide

生成物 1

HCID 88239773benzyl (NE)-N-[[1-[1-(4-fluorophenyl)cyclobutyl]-7-[2-(propylsulfonylamino)ethoxy]-3,4-dihydro-1H-isoquinolin-2-yl]-(phenylmethoxycarbonylamino)methylidene]carbamate

試薬・触媒・溶媒 2

HCID 76223Silver(I) trifluoromethanesulfonate触媒
HCID 6228Dimethylformamide溶媒

実験手順

N-[2-({1-[1-(4-Fluorophenyl)cyclobutyl]-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)ethyl]propane-1-sulfonamide (100 mg, 0.224 mmol, cf. example 65) and dibenzyl [(methylsulfanyl)methylylidene]biscarbamate (104 mg, 0.291 mmol) were dissolved in dry dimethylformamide (1 mL). Triethylamine (0.094 mL, 0.672 mmol) was added followed by silver trifluoromethanesulfonate (81 mg, 0.313 mmol). A yellow precipitate was formed and the reaction mixture turned dark brown. Stirring was continued at room temperature for 3 h. The solvent was evaporated in vacuo. Dichloromethane (15 mL) was added, the solid was removed by filtration and washed with dichloromethane. The combined dichloromethane phases were concentrated in vacuo and the crude product was purified by flash chromatography (silica, dichloromethane then dichlorometane:methanol=100:1). Yield: 100 mg (0.132 mmol, 59%).

後処理

  1. customA yellow precipitate was formed
  2. customThe solvent was evaporated in vacuo
  3. additionDichloromethane (15 mL) was added
  4. customthe solid was removed by filtration
  5. washwashed with dichloromethane
  6. concentrationThe combined dichloromethane phases were concentrated in vacuo
  7. customthe crude product was purified by flash chromatography (silica, dichloromethane

出典と根拠

ORDレコード
ord-11dd08a0d9e3423a983b1295885af3ff
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08653100B2

反応ノート

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