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Guaiacol → (2S)-2-methoxy-3-{4-[2-(2-methoxy-phenoxy)-ethoxy]-phenyl}-propionic acid

HRID 459332
Notes
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Reaction equation

HRID 459332 reaction equation
C([O:3][C:4](=[O:19])[C@@H:5]([O:17][CH3:18])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15]Br)=[CH:9][CH:8]=1)C.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[OH:28].CO[C@@H](CC1C=CC(OCCCOC2C=CC=CC=2)=CC=1)C(O)=O>>[CH3:18][O:17][C@@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][O:28][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[O:21][CH3:20])=[CH:11][CH:12]=1)[C:4]([OH:3])=[O:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 460GuaiacolHCID 58822865(2S)-3-[4-(2-bromo-ethoxy)-phenyl]2-methoxy-propionic acid ethyl esterHCID 58822897(2S)-2-methoxy-3-[4-(3-phenoxy propoxy)-phenyl]-propionic acid

Product 1

HCID 58822608(2S)-2-methoxy-3-{4-[2-(2-methoxy-phenoxy)-ethoxy]-phenyl}-propionic acid

Procedure

The title compound was prepared from (2S)-3-[4-(2-bromo-ethoxy)-phenyl]-2-methoxy-propionic acid ethyl ester (Example 283, Step 2) and 2-methoxy-phenol via the same procedure used for the preparation of (2S)-2-methoxy-3-[4-(3-phenoxy-propoxy)-phenyl]-propionic acid (Example 285, Step 1), to produce a white solid. MS (ES) for C19H22O6 [M+Na]+: 369.4.

Workup

  1. customto produce a white solid

Sources & evidence

ORD record
ord-fee0fd7e5f274be79a2058c6acca2541
Source dataset
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07192982B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes