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

HRID 459331
Notes
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Reaction equation

HRID 459331 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.[OH:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[C:23]#[N:24].CO[C@@H](CC1C=CC(OCCCOC2C=CC=CC=2)=CC=1)C(O)=O>>[C:23]([C:22]1[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=1[O:20][CH2:15][CH2:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][C@H:5]([O:17][CH3:18])[C:4]([OH:3])=[O:19])=[CH:12][CH:11]=1)#[N:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 119072-HydroxybenzonitrileHCID 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 58822691(2S)-3-{4-[2-(2-cyano-phenoxy)-ethoxy]-phenyl}-2-methoxy-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-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-bb5555ad79304a4d994a815925feda41
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