Methyl Salicylate → (2S)-2-{2-[4-(2-carboxy-2-methoxy-ethyl)-phenoxy]-ethoxy}-benzoic acid

HRID 459334

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

Participants

Reactant 3

HCID 4133Methyl Salicylate

HCID 58822865(2S)-3-[4-(2-bromo-ethoxy)-phenyl]2-methoxy-propionic acid ethyl ester

HCID 58822897(2S)-2-methoxy-3-[4-(3-phenoxy propoxy)-phenyl]-propionic acid

Product 1

HCID 58822898(2S)-2-{2-[4-(2-carboxy-2-methoxy-ethyl)-phenoxy]-ethoxy}-benzoic 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-hydroxy-benzoic acid methyl ester 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 colorless oil. MS (ES) for C19H20O7 [M+Na]+: 383.3.

Workup

customto produce a colorless oil

Sources & evidence

ORD record: ord-839c6db9b8da4b1eb3e421bf2a321484
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192982B2

Linked notes

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