(R)-ethoxy-(2-fluoro-4-methoxy-phenyl)-acetic acid → HCID 178468204, compound

HRID 1247441Notes

Reaction equation

HRID 1247441 reaction equation
[CH2:1]([O:3][C@H:4]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[F:16])[C:5]([OH:7])=O)[CH3:2].Cl.[CH2:18]([O:25][C:26](=[O:38])[N:27]=[C:28]([NH2:37])[C:29]1[CH:34]=[CH:33][C:32]([CH2:35][NH2:36])=[CH:31][CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:18]([O:25][C:26](=[O:38])/[N:27]=[C:28](/[NH2:37])\[C:29]1[CH:30]=[CH:31][C:32]([CH2:35][NH:36][C:5](=[O:7])[C@H:4]([O:3][CH2:1][CH3:2])[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=2[F:16])=[CH:33][CH:34]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 69290932(R)-ethoxy-(2-fluoro-4-methoxy-phenyl)-acetic acidHCID 69291995[(4-Aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester hydrochloride

Product 1

HCID 178468204HCID 178468204, compound

Procedure

According to general procedure B (R)-ethoxy-(2-fluoro-4-methoxy-phenyl)-acetic acid was reacted with [amino-(4-aminomethyl-phenyl)-methylene]-carbamic acid benzyl ester hydrochloride 1:2 (prepared according to Ch. Lila, Ph. Gloanec, L. Cadet, Y. Hervé, J. Fournier, F. Leborgne, T. J. Verbeuren, G. De Nanteuil, Synthetic Communications 1998, 28, 23, 4419–4429) to give [1-amino-1-(4-{[(R)-2-ethoxy-2-(2-fluoro-4-methoxy-phenyl)-acetylamino]-methyl}-phenyl)-meth-(E)-ylidene]-carbamic acid benzyl ester (96.5% ee). Off-white solid.

Sources & evidence

ORD record
ord-df317405b14c445a928570afa4d26a9a
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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