Water → HCID 178474735, Verbindung

HRID 579586

Reaktionsgleichung

Reaktionsgleichung von HRID 579586
[C:1]([NH:4][C:5]([C@@H:17]1[CH2:20][C@H:19]([N:21]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:18]1)([CH2:13][CH2:14][CH:15]=[CH2:16])[C:6]([NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:3])[CH3:2].[CH3:36][C:37]1([CH3:44])[C:41]([CH3:43])([CH3:42])[O:40][BH:39][O:38]1.O>ClCCl.[Ir+].ClC1CCC=CCCC=1.C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([NH:4][C:5]([C@@H:17]1[CH2:18][C@H:19]([N:21]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:20]1)([CH2:13][CH2:14][CH2:15][CH2:16][B:39]1[O:40][C:41]([CH3:43])([CH3:42])[C:37]([CH3:44])([CH3:36])[O:38]1)[C:6]([NH:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7])(=[O:3])[CH3:2]

Komponenten

7

Edukt 3

HCID 962WaterHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 178446405HCID 178446405, Verbindung

Produkt 1

HCID 178474735HCID 178474735, VerbindungAusbeute 74,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 742671,2-Bis(diphenylphosphino)ethaneKatalysatorHCID 178478077HCID 178478077, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

After stirring for 30 min, a solution of cis-tert-butyl 3-(2-acetamido-1-(tert-butylamino)-1-oxohex-5-en-2-yl)cyclobutyl(benzyl)carbamate (5.34 g, 10.5 mmol), chloro-1,5-cyclooctadiene iridium(I) dimer (212 mg, 0.32 mmol, 3 mol %) and 1,2-bis(diphenylphosphino)ethane (252 mg, 0.63 mmol, 6 mol %) in dichloromethane (50 mL) was cooled to 0° C. and carefully treated with 4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (3.1 mL, 21.1 mmol, 2 eq) over 5 min. After slowly warming to room temperature and stirring overnight, the reaction was poured into water and extracted with ethyl acetate (3×). The combined organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated. Purification by flash column chromatography (silica gel, 10-40% ethyl acetate in heptane) gave cis-tert-butyl 3-(2-acetamido-1-(tert-butylamino)-1-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexan-2-yl)cyclobutyl(benzyl)carbamate (4.8 g, 7.83 mmol, 74%). ESI MS found for C34H56BN3O6 m/z [614.2 (M+1), 636.2 (M+23)].

Aufarbeitung

  1. stirringstirring overnight
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic phase was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (silica gel, 10-40% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-145b60898c134376ae3964236b0ea64a
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040703B2

Verknüpfte Notizen

Wird geladen…