Water → (2S)-3-(4-benzyloxy-phenyl)-2-propoxy-propionic acid ethyl ester

HRID 459398ノート

反応式

HRID 459398 の反応式
[CH2:1](I)[CH2:2][CH3:3].[CH2:5]([O:7][C:8](=[O:26])[C@@H:9]([OH:25])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)[CH3:6].C(OCC)(=O)C.O>CN(C=O)C.[Ag]=O>[CH2:5]([O:7][C:8](=[O:26])[C@@H:9]([O:25][CH2:1][CH2:2][CH3:3])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:13][CH:12]=1)[CH3:6]

参加物

7

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 336431-IodopropaneHCID 22978911(S)-ethyl 3-(4-(benzyloxy)phenyl)-2-hydroxypropanoate

生成物 1

HCID 58822945(2S)-3-(4-benzyloxy-phenyl)-2-propoxy-propionic acid ethyl ester

試薬・触媒・溶媒 2

HCID 92152Silver(II) oxide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

Propyl iodide (41.6 mmol) was added at room temperature to a solution of (2S)-3-(4-benzyloxy-phenyl)-2-hydroxy-propionic acid ethyl ester (Example 377, Step 2) (8.3 mmol) and silver oxide (12.45 mmol) in 40 mL of DMF. The mixture was heated at 50° C. for 24 hours. After that the mixture was cooled to room temperature, 300 ml of ethyl acetate and 200 ml of water were added. The aqueous layer was separated and the organic layer were washed with brine (3×100 ml), and then dried over (MgSO4), filtered and concentrated under vacuum. The crude was purified by chromatography (silica gel, hexanes/ethyl acetate 6:1) to produce a yellow oil. 1H-NMR (CDCl3, 200.15 MHz): 7.42–7.31 (m, 5 H), 7.17 (d, 2 H, J=8.6 Hz), 6.90 (d, 2 H, J=8.6 Hz), 5.05 (s, 2 H), 4.17 (q, 2 H, J=7.0 Hz), 3.97 (dd, 1 H, J=7.0, 6.2 Hz), 3.53 (dt, 1 H, J=8.9, 6.4 Hz), 3.23 (dt, 1 H, J=9.1, 6.7 Hz), 2.97 (d, 2 H, J=6.7 Hz), 1.66–1.48 (m, 2 H), 1.23 (t, 3 H, J=7.3 Hz), 0.86 (t, 3 H, J=7.5 Hz).

後処理

  1. temperatureAfter that the mixture was cooled to room temperature
  2. customThe aqueous layer was separated
  3. washthe organic layer were washed with brine (3×100 ml)
  4. dry with materialdried over (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude was purified by chromatography (silica gel, hexanes/ethyl acetate 6:1)
  8. customto produce a yellow oil

出典と根拠

ORDレコード
ord-1735de6a00cb4820abfda44e3cf302e5
出典データセット
uspto-grants-2007_03
特許番号
US07192982B2

反応ノート

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