Triethylamine → HCID 10174570, Verbindung

HRID 1610994Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1610994
C([NH:4][CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[C:10]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[Cl:32])[C:6]([OH:8])=[O:7])(=O)C.C(N(CC)CC)C.C1C=NC2N(O)N=NC=2C=1.[F:50][CH:51]([F:55])[C:52](O)=[O:53].CCN=C=NCCCN(C)C>C(Cl)Cl.CCOC(C)=O>[Cl:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][O:24][C:10]1[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[CH:12][CH:13]=[CH:14][C:9]=1[CH:5]([NH:4][C:52](=[O:53])[CH:51]([F:55])[F:50])[C:6]([OH:8])=[O:7]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 9788Difluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 10151939HCID 10151939, Verbindung

Produkt 1

HCID 10174570HCID 10174570, VerbindungAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of Example 13 Part A compound (222 mg, 0.45 mmol) under argon at room temperature in CH2Cl2 (2.5 mL) was added triethylamine (85 μL, 0.6 mmol), HOAt (69 mg, 0.5 mmol) and difluoroacetic acid (48 mg, 0.5 mmol) was added EDAC (96 mg, 0.5 mmol). After 16 h, the reaction mixture was diluted with EtOAc, washed once with 10% citric acid, dried (MgSO4) and evaporated. Purification by flash chromatography on silica gel provided the title compound as a colorless oil, 156 mg (64% yield). LC/MS gave the correct molecular ion [(M+H)+=538] for the desired compound.

Aufarbeitung

  1. washwashed once with 10% citric acid
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customPurification by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-04c91fa03c6a4c6b811ba95590ff410e
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06984645B2

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