Diethylamine → methyl (2S)-5-(4-bromophenyl)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-4-pentynoate

HRID 2264822ノート

反応式

HRID 2264822 の反応式
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]#[CH:16])[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])[CH3:3].I[C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=1.C(NCC)C.C(OCC)(=O)C>C(OCC)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([C:16]#[C:15][CH2:14][C@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:10]([O:12][CH3:13])=[O:11])=[CH:19][CH:20]=1

参加物

8

反応物 4

HCID 8021DiethylamineHCID 8857Ethyl AcetateHCID 115221-Bromo-4-iodobenzeneHCID 11817013(S)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-ynoate

生成物 1

HCID 59596703methyl (2S)-5-(4-bromophenyl)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-4-pentynoate収率 69.9%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 3283Diethyl Ether溶媒

実験手順

A solution of methyl (2S)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-4-pentynoate (D64, 1.020 g, 4.49 mmol), prepared by an analogous procedure to the one described hereinabove, 4-Iodo-bromobenzene (1.524 g, 5.38 mmol), diethylamine (2.28 ml, 1.62 g, 22.12 mmol), CuI (84 mg, 0.441 mmol) and Pd(PPh3)2Cl2 (156 mg, 0.22 mmol) in diethyl ether (10 ml) was stirred at room temperature for 24 h. Ethyl acetate was added and the organic layer was washed with aqueous ammonium chloride solution, dried (Na2SO4), filtered and evaporated under vacuum. The residue was purified via flash chromatography using a gradient of cyclohexanes and ethyl acetate (98:2 to 80:20) to afford the title compound (1.199 g, 69%). MS: (ES/+) m/z: 404, 406 [MH+], C17H20BrNO4 requires 404. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 7.56 (d, 1H), 7.45 (d, 1H), 7.32 (d, 1H), 4.30 (m, 1H), 3.67 (s, 3H), 2.82 (m, 2H), 1.40 and 1.38 (2xs, 9H).

後処理

  1. washthe organic layer was washed with aqueous ammonium chloride solution
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated under vacuum
  5. customThe residue was purified via flash chromatography

出典と根拠

ORDレコード
ord-2f4e2deb04994c1e92b764f67b4699be
出典データセット
uspto-grants-2010_12
特許番号
US07855218B2

反応ノート

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