Pyridine → HCID 145857710、化合物

HRID 723223ノート

反応式

HRID 723223 の反応式
Cl[C:2](OC1C=CC([N+]([O-])=O)=CC=1)=[O:3].[CH3:14][Si:15]([CH3:57])([CH3:56])[CH2:16][CH2:17][O:18][C:19](=[O:55])[NH:20][C:21]1[CH:26]=[C:25]([CH3:27])[C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([S:34]([C:37]3[CH:41]=[C:40]([C:42]([NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=[NH:43])[S:39][C:38]=3[S:52][CH3:53])(=[O:36])=[O:35])[CH:29]=2)=[C:23]([NH2:54])[CH:22]=1.N1C=CC=CC=1.[CH3:64][O:65][C:66](=[O:80])[C:67]1[CH:72]=[CH:71][C:70]([O:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][NH2:79])=[CH:69][CH:68]=1>C(Cl)Cl.CCOC(C)=O.C(N(CC)CC)C>[CH3:64][O:65][C:66](=[O:80])[C:67]1[CH:68]=[CH:69][C:70]([O:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][NH:79][C:2]([NH:54][C:23]2[CH:22]=[C:21]([NH:20][C:19]([O:18][CH2:17][CH2:16][Si:15]([CH3:14])([CH3:56])[CH3:57])=[O:55])[CH:26]=[C:25]([CH3:27])[C:24]=2[C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([S:34]([C:37]3[CH:41]=[C:40]([C:42]([NH:44][C:45]([O:47][C:48]([CH3:50])([CH3:51])[CH3:49])=[O:46])=[NH:43])[S:39][C:38]=3[S:52][CH3:53])(=[O:35])=[O:36])[CH:29]=2)=[O:3])=[CH:71][CH:72]=1

参加物

8

反応物 4

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 57532225Methyl 4-[(5-aminopentyl)oxy]benzoateHCID 145857641HCID 145857641、化合物

生成物 1

HCID 145857710HCID 145857710、化合物収率 66.5%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

4-Nitrophenyl chloroformate (99.2 mg, 0.49 mmol) was added to a solution of {2-amino-3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-biphenyl-4-yl}-carbamic acid 2-trimethylsilanyl-ethyl ester (303 mg, 0.45 mmol, Example 294: step f) and pyridine (39.8 μL, 0.49 mmol) in methylene chloride (5 mL) at rt. The reaction mixture was stirred for 2 hrs at rt. 4-(5-Amino-pentyloxy)-benzoic acid methyl ester (117 mg, 0.49 mmol, Example 283: step b) and triethylamine were added to the reaction mixture and stirred for 2 hrs at rt. The reaction mixture was diluted in EtOAc, washed with water and brine, and dried over magnesium sulfate. Removal of solvents in vacuo was followed by flash chromatography (50–60% EtOAc/hexanes) to afford the title compound as a yellow solid (280 mg, 66.5%). ESI-MS (m/z): Calcd. for C44H57N5O10S3Si: 940.3 (M+1); found: 939.9.

後処理

  1. stirringstirred for 2 hrs at rt
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customRemoval of solvents in vacuo

出典と根拠

ORDレコード
ord-957a5254deeb43fabf601b368dff6b78
出典データセット
uspto-grants-2006_11
特許番号
US07138530B2

反応ノート

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