1-Phenethylamine → (2S)-2-methoxy-3-{4-[(1-Phenyl-ethylcarbamoyl)-methoxy]-phenyl}-propionic acid

HRID 1353252

Reaction equation

HRID 1353252 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][C:15]([OH:17])=O)=[CH:9][CH:8]=1)C.[C:21]1([CH:27]([NH2:29])[CH3:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O[C@@H](CC1C=CC(O[C@@H](C(=O)NCCC2C=CC(OC3C=CC=CC=3)=CC=2)C)=CC=1)C(O)=O)C>>[CH3:19][O:18][C@@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][C:15](=[O:17])[NH:29][CH:27]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:28])=[CH:11][CH:12]=1)[C:4]([OH:3])=[O:20]

Participants

4

Reactant 3

HCID 74081-PhenethylamineHCID 9847886(2S,1R)-2-ethoxy-3-(4-{1-[2-(4-phenoxy-phenyl)-ethylcarbamoyl]-ethoxy}-phenyl)propionic acidHCID 58864673(2S)-3-(4-carboxymethoxy-phenyl)-2-methoxy-propionic acid ethyl ester

Product 1

HCID 11725864(2S)-2-methoxy-3-{4-[(1-Phenyl-ethylcarbamoyl)-methoxy]-phenyl}-propionic acid

Procedure

The title compound was prepared from (2S)-3-(4-carboxymethoxy-phenyl)-2-methoxy-propionic acid ethyl ester (PREPARATION 3, step 2) and 1-phenyl-ethylamine via the same procedure used for the preparation of (2S,1R)-2-ethoxy-3-(4-{1-[2-(4-phenoxy-phenyl)-ethylcarbamoyl]-ethoxy}-phenyl)-propionic acid (Example 1, step 3) to produce a yellow oil. MS (ES) For C20H23NO5 [M+H]+: 358.

Workup

  1. customto produce a yellow oil

Sources & evidence

ORD record
ord-42666471d10845a59bbcb41c8d2bb7b0
Source dataset
uspto-grants-2007_05
Patent number
US07220880B2

Linked notes

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