Hydrochloric Acid → HCID 69544405、化合物

HRID 480278ノート

反応式

HRID 480278 の反応式
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:6][CH:5]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:29](Br)[CH:30]=[CH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.Cl>CN(C=O)C>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][N:13]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:29]/[CH:30]=[CH:31]/[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:6][CH:5]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 98116BromomethylstyreneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 54008307HCID 54008307、化合物

生成物 1

HCID 69544405HCID 69544405、化合物収率 78.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-(2-methanesulfonylamino-ethoxy)-benzoic acid methyl ester (62 mg, 0.23 mmol) in DMF (10 mL) at 0° C. was added sodium bis(trimethylsilyl)amide (1.0M in THF, 0.24 mL, 0.24 mmol) dropwise. After 20 minutes, cinnamyl bromide (51 mg, 0.26 mmol) was added and the reaction was stirred at room temperature for 2 h. Aqueous 1N HCl was added and the product was extracted into EtOAc. The organic solution was washed with 1N HCl (3×) followed by brine. The organic solution was dried (Na2SO4), filtered, and concentrated. Radial chromatography (20% EtOAc in hexanes) provided trans4-{2-[methanesulfonyl-(3-phenyl-allyl)-amino]-ethoxy}-benzoic acid methyl ester (70 mg). 1NMR (400 MHz, CDCl3) δ 7.97 (d, 2H), 7.35-7.23 (m, 5H), 6.88 (d, 2H), 6.58 (d, 1H), 6.18 (m, 1H), 4.20 (t, 2H), 4.12 (d, 2H), 3.88 (s, 3H), 3.68 (t, 2H), 2.95 (s, 3H).

後処理

  1. extractionthe product was extracted into EtOAc
  2. washThe organic solution was washed with 1N HCl (3×)
  3. dry with materialThe organic solution was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-e7ad5260828e4571b0f7803fa7924d7d
出典データセット
uspto-grants-2003_11
特許番号
US06649657B2

反応ノート

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