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Diisopropylethylamine → Biphenyl-2-ylcarbamic Acid 1-[2-[(4-{[2-(3-{(R)-2-{(R)-2-(8-Benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)-ethylamino]propyl}phenyl)ethylcarbamoyl]methyl}phenyl)-methylcarbamoyl]ethyl}piperidin-4-yl Ester

HRID 1097077
ノート
印刷プレビュー

反応式

HRID 1097077 の反応式
[NH2:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH2:10][C@H:11]([NH:13][CH2:14][C@@H:15]([C:24]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[C:30]3[C:25]=2[CH:26]=[CH:27][C:28](=[O:42])[NH:29]3)[O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH3:12])[CH:7]=[CH:8][CH:9]=1.[C:43]1([C:75]2[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=2)[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[NH:49][C:50]([O:52][CH:53]1[CH2:58][CH2:57][N:56]([CH2:59][CH2:60][C:61](CNC2C=CC(CC(O)=O)=CC=2)=[O:62])[CH2:55][CH2:54]1)=[O:51].[O-]S(C(F)(F)F)(=O)=O.C([N:92]([CH2:96]C)[CH:93]([CH3:95])[CH3:94])(C)C>C(Cl)Cl>[CH2:35]([O:34][C:31]1[CH:32]=[CH:33][C:24]([C@@H:15]([O:16][Si:17]([C:20]([CH3:21])([CH3:23])[CH3:22])([CH3:19])[CH3:18])[CH2:14][NH:13][C@H:11]([CH3:12])[CH2:10][C:6]2[CH:5]=[C:4]([CH2:3][CH2:2][NH:1][C:15]([CH2:24][C:25]3[CH:30]=[CH:94][C:93]([N:92]([CH3:96])[C:61]([CH2:60][CH2:59][N:56]4[CH2:57][CH2:58][CH:53]([O:52][C:50](=[O:51])[NH:49][C:44]5[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=5[C:75]5[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=5)[CH2:54][CH2:55]4)=[O:62])=[CH:95][CH:26]=3)=[O:16])[CH:9]=[CH:8][CH:7]=2)=[C:25]2[C:30]=1[NH:29][C:28](=[O:42])[CH:27]=[CH:26]2)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=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 4

HCID 81531DiisopropylethylamineHCID 2758875TrifluoromethanesulfonateHCID 667815115-[(R)-2-{(R)-2-[3-(2-Aminoethyl)phenyl]-1-methylethylamino}-1-(tert-butyldimethylsilanyloxy)ethyl]-8-benzyloxy-1H-quinolin-2-oneHCID 66781677[4-({3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionyl}methylamino)-phenyl]acetic acid

生成物 1

HCID 86704962
Biphenyl-2-ylcarbamic Acid 1-[2-[(4-{[2-(3-{(R)-2-{(R)-2-(8-Benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)-ethylamino]propyl}phenyl)ethylcarbamoyl]methyl}phenyl)-methylcarbamoyl]ethyl}piperidin-4-yl Ester
収率 76.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 5-[(R)-2-{(R)-2-[3-(2-aminoethyl)phenyl]-1-methylethylamino}-1-(tert-butyldimethylsilanyloxy)ethyl]-8-benzyloxy-1H-quinolin-2-one (0.586 g, 1.00 mmol); [4-({3-[4-(biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionyl}methylamino)phenyl]acetic acid (0.516 g, 1.00 mmol); 2-chloropyridium triflate on Wang resin (polymer-supported Mukaiyama reagent) (1.19 mmol/g loading; 1.68 g, 2.00 mmol); and N,N-diisopropylethylamine (522 μL, 3.00 mmol) in DCM (5.00 mL) was stirred at room temperature overnight. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-5% MeOH in DCM) to give the title compound (412 mg, 38% yield) as an off-white oil.

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (0-5% MeOH in DCM)

出典と根拠

ORDレコード
ord-177e4e5d23874521a9bb689fd3d22284
出典データセット
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08138345B2

反応ノート

読み込み中…

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