Ethyl 1-(4-iodobutyl)-1-cyclobutanecarboxylate → Ethyl 11-[1-(ethoxycarbonyl)cyclobutyl]-2,2-dimethyl-7-oxoundecanoate

HRID 239045

Reaktionsgleichung

Reaktionsgleichung von HRID 239045
C(OC(=O)C(C)(C)CCCCC([N+]#C)S(C1C=CC(C)=CC=1)(=O)=O)C.I[CH2:27][CH2:28][CH2:29][CH2:30][C:31]1([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:34][CH2:33][CH2:32]1.CC([O-])(C)C.[K+].[C:46]([O:50][C:51]([C:53]1([CH2:56][CH2:57][CH2:58][CH2:59][C:60](=[O:75])CCCCC2(C(OC(C)(C)C)=O)CC2)[CH2:55][CH2:54]1)=[O:52])(C)(C)[CH3:47]>Cl>[CH2:38]([O:37][C:35]([C:31]1([CH2:30][CH2:29][CH2:28][CH2:27][C:60](=[O:75])[CH2:59][CH2:58][CH2:57][CH2:56][C:53]([CH3:55])([CH3:54])[C:51]([O:50][CH2:46][CH3:47])=[O:52])[CH2:34][CH2:33][CH2:32]1)=[O:36])[CH3:39]

Komponenten

6

Edukt 4

HCID 21932017Ethyl 1-(4-iodobutyl)-1-cyclobutanecarboxylateHCID 21932031t-Butyl 1-[9-[1-(tert-butoxycarbonyl)cyclopropyl]-5-oxononyl]-1-cyclopropanecarboxylateHCID 21932083{7-Ethoxy-6,6-dimethyl-1-[(4-methylphenyl)sulfonyl]-7-oxoheptyl}(methylidyne)ammoniumHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 68579358Ethyl 11-[1-(ethoxycarbonyl)cyclobutyl]-2,2-dimethyl-7-oxoundecanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

Compound 106e was prepared likewise Method C starting from 108a (11.01 g, 30.1 mmol), 105b (10.28 g, 33.1 mmol) and KOtBu (4.06 g, 36.2 mmol) to give, after purification by column chromatography (silica, heptane:EtOAc=6:1; a layer of NaHCO3 was put on the base of the column), ethyl 1-[11-ethoxy-5-isocyano-10,10-dimethyl-5-[(4-methylphenyl)sulfonyl]-11-oxoundecyl]-1-cyclobutanecarboxylate (14.11 g) as a colorless oil. Part of this oil (13.86 g, 25.3 mmol) was treated with cone aqueous HCl (50 mL), as described for 106d, to give crude 106e, which was stirred up in heptane (50 mL) and the resulting precipitate was filtered off and washed with heptane (3×50 mL). The combined filtrates were washed with aqueous NaOH (1M, 2×50 mL) and brine (50 mL) and dried to give 106e (9.44 g, >90% pure by 1H NMR, 75%) as a slightly yellow oil. 1H NMR: δ 4.12 (q, J=7.1 Hz, 2H), 4.09 (q, J=7.1 Hz, 2H), 2.50-2.29 (m, 2H), 2.37 (t, J=7.4 Hz, 4H), 1.95-1.70 (m, 6H), 1.61-1.44 (m, 6H), 1.30-1.09 (m, 4H), 1.25 (t, J=7.1 Hz, 3H), 1.24 (t, J=7.1 Hz, 3H), 1.14 (s, 6H). 13C NMR: δ 210.1, 177.3, 176.6, 60.1 (2×), 47.5, 42.57 (2×), 42.1, 40.4, 37.8, 30.0 (2×), 25.2 (2×), 24.7, 24.6, 24.2, 24.1, 15.7, 14.4, 14.3.

Aufarbeitung

  1. customCompound 106e was prepared likewise Method C
  2. customto give
  3. customafter purification by column chromatography (silica, heptane

Quellen und Nachweise

ORD-Eintrag
ord-9c6119fe919c4394b2e71d6205a218bf
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642653B2

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