2-Hydroxybenzonitrile → (2S)-3-{4-[3-(2-cyano-phenoxy)-propoxy]-phenyl}-2-methoxy-propionic acid

HRID 459318

Reaction equation

HRID 459318 reaction equation
C([O:3][C:4](=[O:20])[C@@H:5]([O:18][CH3:19])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16]Br)=[CH:9][CH:8]=1)C.[OH:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[C:24]#[N:25].CO[C@@H](CC1C=CC(OCCCOC2C=CC=CC=2)=CC=1)C(O)=O>>[C:24]([C:23]1[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=1[O:21][CH2:16][CH2:15][CH2:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][C@H:5]([O:18][CH3:19])[C:4]([OH:3])=[O:20])=[CH:12][CH:11]=1)#[N:25]

Participants

4

Reactant 3

HCID 119072-HydroxybenzonitrileHCID 58822859(2S)-3-[4-(3-Bromopropoxy)-phenyl]-2-methoxy-propionic acid ethyl esterHCID 58822897(2S)-2-methoxy-3-[4-(3-phenoxy propoxy)-phenyl]-propionic acid

Product 1

HCID 58822779(2S)-3-{4-[3-(2-cyano-phenoxy)-propoxy]-phenyl}-2-methoxy-propionic acid

Procedure

The title compound was prepared from (2S)-3-[4-(3-bromo-propoxy)-phenyl]-2-methoxy-propionic acid ethyl ester (Example 284, Step 2) and 2-hydroxy-benzonitrile 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.

Workup

  1. customto produce a colorless oil

Sources & evidence

ORD record
ord-2ef3eb98769a449d8ec8749fbe297dce
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Linked notes

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