(3R)-3-(3-(((2-((1R)-2,2-Dimethylcyclopentyl)-3'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)phenyl)pentanoic acid → Methyl 2-(2,2-dimethylcyclopentyl)-3'-(methyloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662511Notes

Reaction equation

HRID 1662511 reaction equation
CC1(C)CCC[C@H:3]1[C:7]1C=C(COC2C=C([C@H](CC)CC(O)=O)C=CC=2)C=[CH:9][C:8]=1[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=1.[CH3:37][C:38]1([CH3:72])[CH2:42][CH2:41][CH2:40][C@@H:39]1C1C=C(COC2C=C([C@H](CC)CC(O)=O)C=CC=2)C=CC=1C1C=CC=C(OC)C=1.CC1(C)CCC[C@H]1C1C=C(COC2C=C([C@@H:93](CC)[CH2:94][C:95]([OH:97])=[O:96])C=CC=2)C=CC=1C1C=CC=C(OC)C=1.[CH3:109]C1(C)CCC[C@@H]1C1C=C(COC2C=C([C@@H](CC)CC(O)=O)C=CC=2)C=CC=1C1C=CC=C(OC)C=1>>[CH3:72][C:38]1([CH3:37])[CH2:39][CH2:40][CH2:41][CH:42]1[C:9]1[CH:93]=[C:94]([C:95]([O:97][CH3:109])=[O:96])[CH:3]=[CH:7][C:8]=1[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=1

Participants

5

Reactant 4

HCID 57705561(3R)-3-(3-(((2-((1R)-2,2-Dimethylcyclopentyl)-3'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)phenyl)pentanoic acidHCID 57705814(3S)-3-(3-(((2-((1S)-2,2-dimethylcyclopentyl)-3'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)phenyl)pentanoic acidHCID 57706391(3R)-3-(3-(((2-((1S)-2,2-dimethylcyclopentyl)-3'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)phenyl)pentanoic acidHCID 57707128(3S)-3-(3-(((2-((1R)-2,2-dimethylcyclopentyl)-3'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)phenyl)pentanoic acid

Product 1

HCID 57706985Methyl 2-(2,2-dimethylcyclopentyl)-3'-(methyloxy)-1,1'-biphenyl-4-carboxylate

Procedure

(3R)-3-(3-(((2-((1R)-2,2-Dimethylcyclopentyl)-3′-(methyloxy)-1,1′-biphenyl-4-yl)methyl)oxy)phenyl)pentanoic acid or (3R)-3-(3-(((2-((1S)-2,2-dimethylcyclopentyl)-3′-(methyloxy)-1,1′-biphenyl-4-yl)methyl)oxy)phenyl)pentanoic acid or (3S)-3-(3-(((2-((1R)-2,2-dimethylcyclopentyl)-3′-(methyloxy)-1,1′-biphenyl-4-yl)methyl)oxy)phenyl)pentanoic acid or (3S)-3-(3-(((2-((1S)-2,2-dimethylcyclopentyl)-3′-(methyloxy)-1,1′-biphenyl-4-yl)methyl)oxy)phenyl)pentanoic acid (78.5). The title compound was prepared from chloromethyl compound 78.5F or 78.5G derived from 78.5E (peak two from the separation of the racemic alcohol) using the methods described herein. MS ESI (pos.) m/e: 504.2 (M+H2O)+, 509.2 (M+Na)+.

Workup

  1. customfrom the separation of the racemic alcohol)

Sources & evidence

ORD record
ord-13f08cd7cede4e43b8ada659dfb9e610
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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