3-(Aminomethyl)biphenyl → (2S)-3-(4-{1-[(biphenyl-3-ylmethyl)-carbamoyl]-1-methyl-ethoxy}-phenyl)-2-methoxy-propionic acid

HRID 1353235Notes

Reaction equation

HRID 1353235 reaction equation
C([O:3][C:4](=[O:22])[C@@H:5]([O:20][CH3:21])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]([C:17]([OH:19])=O)([CH3:16])[CH3:15])=[CH:9][CH:8]=1)C.[C:23]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][NH2:30])[CH:24]=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>>[C:23]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][NH:30][C:17]([C:14]([CH3:15])([O:13][C:10]2[CH:9]=[CH:8][C:7]([CH2:6][C@H:5]([O:20][CH3:21])[C:4]([OH:3])=[O:22])=[CH:12][CH:11]=2)[CH3:16])=[O:19])[CH:24]=1

Participants

4

Reactant 3

HCID 27603683-(Aminomethyl)biphenylHCID 9847886(2S,1R)-2-ethoxy-3-(4-{1-[2-(4-phenoxy-phenyl)-ethylcarbamoyl]-ethoxy}-phenyl)propionic acidHCID 58646603(2S)-3-[4-(1-carboxy-1-methyl-ethoxy)-phenyl]-2-methoxy-propionic acid ethyl ester

Product 1

HCID 10411340(2S)-3-(4-{1-[(biphenyl-3-ylmethyl)-carbamoyl]-1-methyl-ethoxy}-phenyl)-2-methoxy-propionic acid

Procedure

The title compound was prepared from (2S)-3-[4-(1-carboxy-1-methyl-ethoxy)-phenyl]-2-methoxy-propionic acid ethyl ester (PREPARATION 5, step 2) and C-biphenyl-3-yl-methylamine 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 C27H29NO5 [M−H]−: 446.

Workup

  1. customto produce a colorless oil

Sources & evidence

ORD record
ord-2221d7af6d29499bb88f2f7be0827b0c
Source dataset
uspto-grants-2007_05
Patent number
US07220880B2

Reaction notes

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