1,2-Dichloroethane → HCID 11700153, Verbindung

HRID 1786538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1786538
[CH3:1][N:2]([C@@H:24]1[CH2:28][CH2:27][NH:26][CH2:25]1)[C:3](=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1.[C:29]([C:33]1[CH:34]=[C:35]([CH:39]=[C:40]([C:44]([CH3:47])([CH3:46])[CH3:45])[C:41]=1[O:42][CH3:43])[C:36](O)=[O:37])([CH3:32])([CH3:31])[CH3:30].C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:44]([C:40]1[CH:39]=[C:35]([CH:34]=[C:33]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:41]=1[O:42][CH3:43])[C:36]([N:26]1[CH2:27][CH2:28][C@@H:24]([N:2]([CH3:1])[C:3](=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([C:9]2[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=2)[C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[CH2:25]1)=[O:37])([CH3:47])([CH3:46])[CH3:45]

Komponenten

6

Edukt 3

HCID 111,2-DichloroethaneHCID 22324252HCID 22324252, VerbindungHCID 57597585HCID 57597585, Verbindung

Produkt 1

HCID 11700153HCID 11700153, VerbindungAusbeute 86,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (R)-6,6-Bis-(4-fluoro-phenyl)-hexanoic acid methyl-pyrrolidin-3-yl-amide (0.78 g, 2.02 mmol) in dry CH2Cl2 (30 ml) was added 3,5-di-tert-butyl-4-methoxy benzoic acid (0.53 g, 2.02 mmol) under nitrogen. To the reaction was added EDC (0.77 g, 4.04 mmol) and DMAP (cat) and the reaction mixture stirred under nitrogen at room temperature overnight. The reaction was then concentrated under reduced pressure. The residue was dissolved in ethyl acetate: water (10:1) (150 ml). The organic was washed with water (30 ml, 2×) and 10% NaOH (30 ml) and dried over MgSO4 and evaporated to dryness. The resulting residue was purified by column chromatography using CH2Cl2:CH3OH (15:1) to give 1.1 g of desired product.

Aufarbeitung

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate: water (10:1) (150 ml)
  3. washThe organic was washed with water (30 ml, 2×) and 10% NaOH (30 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe resulting residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f5d8b6a413cc454b9f8f119c04545da2
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07507760B2

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