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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 2412301
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HRID 2412301 반응식
[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
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참가 물질

6

반응물 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

생성물 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
수율 76.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-43a08373c6964da7862d54b5bfd69807
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08816088B2

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