4-Phenoxyphenethylamine → (2S)-2-methoxy-3-(4-{[2-(4-phenoxy-phenyl)-ethylcarbamoyl]-methoxy}-phenyl)-propionic acid

HRID 1353274Notes

Reaction equation

HRID 1353274 reaction equation
C(OC(=O)[C@@H](OC)CC1C=CC(OCC(O)=O)=CC=1)C.O(C1C=CC(CCN)=CC=1)C1C=CC=CC=1.[CH2:37]([O:39][C@@H:40]([CH2:44][C:45]1[CH:50]=[CH:49][C:48]([O:51][C@@H:52]([C:54](=[O:71])[NH:55][CH2:56][CH2:57][C:58]2[CH:63]=[CH:62][C:61]([O:64][C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)=[CH:60][CH:59]=2)C)=[CH:47][CH:46]=1)[C:41]([OH:43])=[O:42])C>>[CH3:37][O:39][C@@H:40]([CH2:44][C:45]1[CH:46]=[CH:47][C:48]([O:51][CH2:52][C:54](=[O:71])[NH:55][CH2:56][CH2:57][C:58]2[CH:59]=[CH:60][C:61]([O:64][C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)=[CH:62][CH:63]=2)=[CH:49][CH:50]=1)[C:41]([OH:43])=[O:42]

Participants

4

Reactant 3

HCID 1455354-PhenoxyphenethylamineHCID 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 58646563(2S)-2-methoxy-3-(4-{[2-(4-phenoxy-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 2-(4-phenoxy-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 C26H27NO6 [M+H]+: 450.

Workup

  1. customto produce a colorless oil

Sources & evidence

ORD record
ord-3f76c3aa76ac4982968ce07f1d2e7731
Source dataset
uspto-grants-2007_05
Patent number
US07220880B2

Reaction notes

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