3-Chlorophenethylamine → (2S)-3-(3-{1-[2-(3-chloro-phenyl)-ethylcarbamoyl]-1-methyl-ethoxy}-phenyl)-2-methoxy-propionic acid

HRID 1353251Notes

Reaction equation

HRID 1353251 reaction equation
C[O:2][C:3](=[O:21])[C@@H:4]([O:19][CH3:20])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]([C:16]([OH:18])=O)([CH3:15])[CH3:14])[CH:7]=1.[Cl:22][C:23]1[CH:24]=[C:25]([CH2:29][CH2:30][NH2:31])[CH:26]=[CH:27][CH:28]=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>>[Cl:22][C:23]1[CH:24]=[C:25]([CH2:29][CH2:30][NH:31][C:16]([C:13]([CH3:14])([O:12][C:8]2[CH:7]=[C:6]([CH2:5][C@H:4]([O:19][CH3:20])[C:3]([OH:2])=[O:21])[CH:11]=[CH:10][CH:9]=2)[CH3:15])=[O:18])[CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 3

HCID 1393813-ChlorophenethylamineHCID 9847886(2S,1R)-2-ethoxy-3-(4-{1-[2-(4-phenoxy-phenyl)-ethylcarbamoyl]-ethoxy}-phenyl)propionic acidHCID 58646552HCID 58646552, compound

Product 1

HCID 10093556(2S)-3-(3-{1-[2-(3-chloro-phenyl)-ethylcarbamoyl]-1-methyl-ethoxy}-phenyl)-2-methoxy-propionic acid

Procedure

The title compound was prepared from (2S)-3-[3-(1-carboxy-1-methyl-ethoxy)-phenyl]-2-methoxy-propionic acid methyl ester (EXAMPLE 56, step 2) and 2-(3-chloro-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 colorless oil. MS (ES) for C22H29ClNO5 [M−H]−: 418.

Workup

  1. customto produce a colorless oil

Sources & evidence

ORD record
ord-243e99ba42be45ecaced30ba2dc56728
Source dataset
uspto-grants-2007_05
Patent number
US07220880B2

Reaction notes

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