N-(Phenylmethyl)-beta-alanine ethyl ester → (2S)-3-(4-{[benzyl-(2-ethoxycarbonyl-ethyl)-carbamoyl]-methoxy}-phenyl)-2-methoxy-propionic acid

HRID 1353225Notes

Reaction equation

HRID 1353225 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.[CH2:21]([O:23][C:24](=[O:35])[CH2:25][CH2:26][NH:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH3:22].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>>[CH2:28]([N:27]([CH2:26][CH2:25][C:24]([O:23][CH2:21][CH3:22])=[O:35])[C:15]([CH2:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][C@H:5]([O:18][CH3:19])[C:4]([OH:3])=[O:20])=[CH:12][CH:11]=1)=[O:17])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 3

HCID 90196N-(Phenylmethyl)-beta-alanine ethyl esterHCID 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 58646600(2S)-3-(4-{[benzyl-(2-ethoxycarbonyl-ethyl)-carbamoyl]-methoxy}-phenyl)-2-methoxy-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 3-benzylamino-propionic acid ethyl ester 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 C24H29NO7 [M+H]+: 444.

Workup

  1. customto produce a colorless oil

Sources & evidence

ORD record
ord-75a76180d3f34942a9bfeba12ad2a94a
Source dataset
uspto-grants-2007_05
Patent number
US07220880B2

Reaction notes

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