5,6,7,8-Tetrahydro-2-naphthol → 2-Methoxy-3-{3-[2-(5,6,7,8-tetrahydro-naphthalen-2-yloxy)-ethoxy]-phenyl}-propionic acid

HRID 459376Notes

Reaction equation

HRID 459376 reaction equation
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[OH:11].C[O:13][C:14](=[O:29])[CH:15]([O:27][CH3:28])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][CH2:25]Br)[CH:18]=1.CO[C@@H](CC1C=CC(OCCCOC2C=CC=CC=2)=CC=1)C(O)=O>>[CH3:28][O:27][CH:15]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][CH2:25][O:11][C:2]2[CH:3]=[CH:4][C:5]3[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=3[CH:1]=2)[CH:18]=1)[C:14]([OH:29])=[O:13]

Participants

4

Reactant 3

HCID 143055,6,7,8-Tetrahydro-2-naphtholHCID 58822897(2S)-2-methoxy-3-[4-(3-phenoxy propoxy)-phenyl]-propionic acidHCID 694234133-[3-(2-Bromo-ethoxy)-phenyl]-2-methoxy-propionic acid methyl ester

Product 1

HCID 184432602-Methoxy-3-{3-[2-(5,6,7,8-tetrahydro-naphthalen-2-yloxy)-ethoxy]-phenyl}-propionic acid

Procedure

The title compound was prepared from 5,6,7,8-tetrahydro-naphthalen-2-ol and 3-[3-(2-bromo-ethoxy)-phenyl]-2-methoxy-propionic acid methyl ester (Example 351, Step 1) 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. MS (ES) for C22H26O5 [M−H]−: 369.2.

Workup

  1. customThe enatiomers were separated by chiral HPLC

Sources & evidence

ORD record
ord-53a29daa455f4b94bc7f681bf3b8e028
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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