Pyridine → HCID 145857710, Verbindung

HRID 2216178Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2216178
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

Komponenten

8

Edukt 4

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 57532225Methyl 4-[(5-aminopentyl)oxy]benzoateHCID 145857641HCID 145857641, Verbindung

Produkt 1

HCID 145857710HCID 145857710, VerbindungAusbeute 66,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4d0f77d3072047438f48bbdfc43560e1
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109354B2

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