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

HRID 459398노트

반응식

HRID 459398 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 92152Silver(II) oxide촉매HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1735de6a00cb4820abfda44e3cf302e5
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192982B2

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