Iodoethane → HCID 69422705, compound

HRID 459267Notes

Reaction equation

HRID 459267 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[C@@H:5]([OH:31])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)=[CH:9][CH:8]=1)[CH3:2].[CH2:33](I)[CH3:34]>ClCCl>[CH2:1]([O:3][C:4](=[O:32])[CH:5]([O:31][CH2:33][CH3:34])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[CH:22][CH:23]=2)=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 69421264HCID 69421264, compound

Product 1

HCID 69422705HCID 69422705, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2S)-2-hydroxy-3-{4-[3-(4-phenoxy-phenoxy)-propoxy]-phenyl}-propionic acid ethyl ester, AgO2 (1.5 eq) and ethyl iodide (excess) in dichloromethane was stirred over 10 days. The crude mixture was filtered through celite and concentrated to dryness. The compound was purified by chromatography to give the title product. 1H-NMR (CDCl3, 200.15 MHz): δ 7.34–7.26 (m, 2H), 7.18–6.82 (m, 11H), 4.18–4.17 (m, 6H), 4.01–3.94 (m, 1H), 3.68–3.53 (m, 1H), 3.43–3.28 (m, 1H), 2.96 (d, 2H, J=6.5), 2.25 (qn, 2H, J=6.2), 1.20 (dt, 6H, J=12.6, 7.3).

Workup

  1. filtrationThe crude mixture was filtered through celite and
  2. concentrationconcentrated to dryness
  3. customThe compound was purified by chromatography

Sources & evidence

ORD record
ord-0aa60692b7a04c72a9e84f45a7f95019
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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