(2S)-3-{4-[2-(biphenyl-4-yloxy)-ethoxy]-phenyl}-2-methoxy-propionic acid → 3-{3-[3-(Biphenyl-4-yloxy)-propoxy]-phenyl}-2-methoxy-propionic acid

HRID 459316Notes

Reaction equation

HRID 459316 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.C[O:19][C:20](=[O:32])[CH:21]([O:30][CH3:31])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=1.C1(C2C=CC=CC=2)C=CC(OCCOC2C=CC(C[C@H](OC)C(O)=O)=CC=2)=CC=1>>[C:9]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][O:29][C:25]2[CH:24]=[C:23]([CH2:22][CH:21]([O:30][CH3:31])[C:20]([OH:32])=[O:19])[CH:28]=[CH:27][CH:26]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 10135109(2S)-3-{4-[2-(biphenyl-4-yloxy)-ethoxy]-phenyl}-2-methoxy-propionic acidHCID 152334631,1'-Biphenyl, 4-(3-bromopropoxy)-HCID 588228023-(3-Hydroxy-phenyl)-2-methoxy-propionic acid methyl ester

Product 1

HCID 184431603-{3-[3-(Biphenyl-4-yloxy)-propoxy]-phenyl}-2-methoxy-propionic acid

Procedure

The title compound was prepared from 4-(3-bromo-propoxy)-biphenyl (Example 291, Step 7) and 3-(3-hydroxy-phenyl)-2-methoxy-propionic acid methyl ester (Example 291, Step 4) (0.3 g, 1.42 mmol) via the same procedure used for the preparation of (2S)-3-{4-[2-(biphenyl-4-yloxy)-ethoxy]-phenyl}-2-methoxy-propionic acid (Example 283, Step 3). The crude material was submitted to chiral HPLC separation to afford the single enantiomer of isomer 1. 1H-NMR (CDCl3, 200.15 MHz): 7.57–7.17 (m, 7H), 6.99 (dd, 2H, J=6.7, 2.2), 6.85–6.80 (m, 3H), 4.19 (dd, 4H, J=13.4, 6.4), 4.03 (dd, 1H, J=7.3, 4.3), 3.40 (s, 3H), 0.14 (dd, 1H, J=14.0, 4.3), 2.98 (dd, 1H, J=14.8, 7.5), 2.28 (qui, 2H, J=5.9).

Workup

  1. customThe crude material was submitted to chiral HPLC separation
  2. customto afford the single enantiomer of isomer 1

Sources & evidence

ORD record
ord-0b09039d9903478a9a07c1f5051df6bf
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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