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

HRID 459398Notes

Reaction equation

HRID 459398 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-1735de6a00cb4820abfda44e3cf302e5
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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