6-Hydroxyquinoline → HCID 18443267, compound

HRID 459369Notes

Reaction equation

HRID 459369 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.[N:20]1[C:29]2[C:24](=[CH:25][C:26]([OH:30])=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1.CO[C@@H](CC1C=CC(OCCCOC2C=CC=CC=2)=CC=1)C(O)=O>>[CH3:18][O:17][CH:4]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH2:14][CH2:15][O:30][C:26]2[CH:25]=[C:24]3[C:29](=[CH:28][CH:27]=2)[N:20]=[CH:21][CH:22]=[CH:23]3)[CH:7]=1)[C:3]([OH:2])=[O:19]

Participants

4

Reactant 3

HCID 113746-HydroxyquinolineHCID 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 18443267HCID 18443267, compound

Procedure

The title compound was prepared from 3-[3-(3-bromo-propoxy)-phenyl]-2-methoxy-propionic acid methyl ester Example 323, Step 1) and quinolin-6-ol 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 C22H23NO5 [M+H]+: 382.2.

Workup

  1. customThe enatiomers were separated by chiral HPLC

Sources & evidence

ORD record
ord-ddb23578c3e74387ac258aac06f73cdd
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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