3,4-Dimethylphenol → 3-{3-[3-(3,4-Dimethyl-phenoxy)-propoxy]-phenyl}-2-methoxy-propionic acid

HRID 459362Notes

Reaction equation

HRID 459362 reaction equation
C[O:2][C:3](=[O:19])[CH:4]([O:17][CH3:18])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH2:14][CH2:15]Br)[CH:7]=1.[CH3:20][C:21]1[CH:22]=[C:23]([OH:28])[CH:24]=[CH:25][C:26]=1[CH3:27].CO[C@@H](CC1C=CC(OCCCOC2C=CC=CC=2)=CC=1)C(O)=O>>[CH3:20][C:21]1[CH:22]=[C:23]([CH:24]=[CH:25][C:26]=1[CH3:27])[O:28][CH2:15][CH2:14][CH2:13][O:12][C:8]1[CH:7]=[C:6]([CH2:5][CH:4]([O:17][CH3:18])[C:3]([OH:2])=[O:19])[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 72493,4-DimethylphenolHCID 588228613-[3-(3-Bromo-propoxy)-phenyl]-2-methoxy-propionic acid methyl esterHCID 58822897(2S)-2-methoxy-3-[4-(3-phenoxy propoxy)-phenyl]-propionic acid

Product 1

HCID 184435963-{3-[3-(3,4-Dimethyl-phenoxy)-propoxy]-phenyl}-2-methoxy-propionic acid

Procedure

The title compound was prepared from 3-[3-(3-bromo-propoxy)-phenyl]-2-methoxy-propionic acid methyl ester (Example 323, Step 1) and 3,4-dimethylphenol via the same procedure used for the preparation of (2S)-2-methoxy-3-[4-(3-phenoxy-propoxy)-phenyl]-propionic acid (Example 285, Step 1). The enatiomers were separated by chiral HPLC. 1H-NMR (CDCl3, 200.15 MHz): 7.18 (d, 1H, J=7.5), 7.02 (d, 1H, J=8.3), 6.84–6.62 (m, 5H), 4.14 (t, 2H, J=6.4), 4.12 (t, 2H, J=5.9), 4.02 (dd, 1H, J=7.3, 4.0), 3.39 (s, 3H), 3.13 (dd, 1H, J=14.2, 4.6), 2.97 (dd, 1H, J=14.0, 7.5), 2.23 (q, 1H, J=6.2.1), 2.22 (s, 3H), 2.18 (s, 3H). MS (ES) for C21H26O5 [M+Na]+: 381.2.

Workup

  1. customThe enatiomers were separated by chiral HPLC

Sources & evidence

ORD record
ord-0ff33d0b20b54022a58b9e5880520d30
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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