Benzoyl chloride → HCID 22258151, Verbindung

HRID 1610993Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1610993
[C:1]([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:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)[C:41]1[CH:46]=[CH:45]C=[CH:43][CH:42]=1>C1COCC1.CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:1]([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:3])[C:2]1[CH:45]=[CH:46][CH:41]=[CH:42][CH:43]=1

Komponenten

7

Edukt 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 10151939HCID 10151939, Verbindung

Produkt 1

HCID 22258151HCID 22258151, VerbindungAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of Example 13 Part A compound (197 mg, 0.4 mmol) under argon at 0-5° C. in THF (1.5 mL) was added triethylamine (0.2 mL, 1.6 mmol), DMAP (2 mg, 0.02 mmol) and benzoyl chloride (70 μL, 0.6 mmol). The reaction mixture was allowed to warm to room temperature and after 15 h, it 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, 161 mg (71% yield). LC/MS gave the correct molecular ion [(M+H)+=564] 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-b2d075cec249440fa14daf6700335230
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06984645B2

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