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

HRID 646791

反応式

HRID 646791 の反応式
[CH2:1]([O:3][C:4](=[O:25])[C:5]([CH3:24])([CH3:23])[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([N+]#C)S(C1C=CC(C)=CC=1)(=O)=O)[CH3:2].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-:44])(C)C.[K+]>Cl>[CH2:38]([O:37][C:35]([C:31]1([CH2:30][CH2:29][CH2:28][CH2:27][C:10](=[O:44])[CH2:9][CH2:8][CH2:7][CH2:6][C:5]([CH3:23])([CH3:24])[C:4]([O:3][CH2:1][CH3:2])=[O:25])[CH2:34][CH2:33][CH2:32]1)=[O:36])[CH3:39]

参加物

5

反応物 3

HCID 21932017Ethyl 1-(4-iodobutyl)-1-cyclobutanecarboxylateHCID 21932083{7-Ethoxy-6,6-dimethyl-1-[(4-methylphenyl)sulfonyl]-7-oxoheptyl}(methylidyne)ammoniumHCID 23665647Potassium tert-butoxide

生成物 1

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

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-ef5216b5ba1e46f88792605dc9069f40
出典データセット
uspto-grants-2010_04
特許番号
US07705177B2

関連ノート

読み込み中…