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Dichloromethane → HCID 89668617, Verbindung

HRID 1482246
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1482246
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:10](=[O:17])[N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:4][CH:3]=1.[C:26]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])(=[O:32])[CH2:27][CH2:28][CH2:29][C:30]#[CH:31].C(N(CC)CC)C.C(Cl)Cl>CN(C=O)C.CCCCCC.C(OCC)(=O)C.[Cu]I.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:21]([O:20][C:19]([NH:18][C@H:9]([C:10](=[O:17])[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:31]#[C:30][CH2:29][CH2:28][CH2:27][C:26]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[CH:3][CH:4]=1)=[O:25])([CH3:24])([CH3:23])[CH3:22]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 109649121,1-Dimethylethyl 5-hexynoateHCID 89668441HCID 89668441, Verbindung

Produkt 1

HCID 89668617HCID 89668617, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator
HCID 6228DimethylformamideLösungsmittel
HCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

tert-Butyl (S)-(3-(4-iodophenyl)-1-oxo-1-(piperidin-1-yl)propan-2-yl)carbamate (Compound SP413, Boc-Phe(4-I)-pip) (6.00 g, 13.09 mmol), tert-butyl hex-5-ynoate (Compound SP423) (4.40 g, 26.2 mmol) and triethylamine (5.47 ml, 39.3 mmol) were dissolved in DMF (60.0 ml), CuI (0.125 g, 0.655 mmol) and Pd(dppf)Cl2.CH2Cl2 (0.538 g, 0.655 mmol) were added and the mixture was stirred at room temperature for 4 hours. The reaction solution was diluted with hexane/ethyl acetate (1/1) and washed with a saturated aqueous ammonium chloride solution and brine. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated under reduced pressure, and the resulting residue was purified by column chromatography (hexane:ethyl acetate=100:0-60:40) to afford the title compound SP425 (6.19 g, 95%).

Aufarbeitung

  1. washwashed with a saturated aqueous ammonium chloride solution and brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customthe resulting residue was purified by column chromatography (hexane:ethyl acetate=100:0-60:40)

Quellen und Nachweise

ORD-Eintrag
ord-9916b4137b7347798b261124a2b51c70
Quelldatensatz
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09409952B2

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