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

HRID 969002Notes

Reaction equation

HRID 969002 reaction equation
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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

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 conc 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.

Workup

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

Sources & evidence

ORD record
ord-b4be44b7739c440190793ad4a29ba8a4
Source dataset
uspto-grants-2007_12
Patent number
US07304093B2

Reaction notes

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