HCID 117600035, compound → HCID 86281946, compound

HRID 1497003Notes

Reaction equation

HRID 1497003 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([O:27][CH3:28])=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]([C:21]3[O:22][C:23]([CH3:26])=[N:24][N:25]=3)[CH2:17][C:18]([OH:20])=[O:19])[CH:11]=2)[CH:9]=1)([CH3:3])[CH3:2]>CCCCCCC.CO>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([O:27][CH3:28])=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C@@H:16]([C:21]3[O:22][C:23]([CH3:26])=[N:24][N:25]=3)[CH2:17][C:18]([OH:20])=[O:19])[CH:11]=2)[CH:9]=1)([CH3:3])[CH3:2].[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([O:27][CH3:28])=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C@H:16]([C:21]3[O:22][C:23]([CH3:26])=[N:24][N:25]=3)[CH2:17][C:18]([OH:20])=[O:19])[CH:11]=2)[CH:9]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 117600035HCID 117600035, compound

Product 2

HCID 86281946HCID 86281946, compoundHCID 117600033HCID 117600033, compound

Reagents, catalysts & solvents 1

HCID 19074130HCID 19074130, compoundSolvent

Procedure

The racemic 3-(5′-Isopropyl-2′-methoxy-biphenyl-3-yl)-3-(5-methyl-[1,3,4]oxadiazol-2-yl)-propionic acid is subjected to chromatography on a chiral column using a heptane-methanol gradient to isolate the pure enantiomers (S)-3-(5′-Isopropyl-2′-methoxy-biphenyl-3-yl)-3-(5-methyl-[1,3,4]oxadiazol-2-yl)-propionic acid and (R)-3-(5′-Isopropyl-2′-methoxy-biphenyl-3-yl)-3-(5-methyl-[1,3,4]oxadiazol-2-yl)-propionic acid. The configuration on the chiral carbon atom is arbitrarily assigned (S) to the enantiomer with the shortest retention time on the applied chiral column and (R) to the enantiomer with the longest retention time on the applied chiral column.

Sources & evidence

ORD record
ord-c2996fbf9f4a4de98401f624de2d8096
Source dataset
uspto-grants-2015_12
Patent number
US09199947B2

Reaction notes

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