(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 1662512Notes

Reaction equation

HRID 1662512 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-((1S)-2,2-Dimethylcyclopentyl)-3′-(methyloxy)-1,1′-biphenyl-4-yl)methyl)oxy)phenyl)pentanoic acid or (3R)-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 or (3S)-3-(3-(((2-((1R)-2,2-dimethylcyclopentyl)-3′-(methyloxy)-1,1′-biphenyl-4-yl)methyl)oxy)phenyl)pentanoic acid (78.6). The title compound was prepared from chloromethyl compound 78.5F or 78.5G derived from 78.5D (peak one 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-efb0e4b76ddb4cad9bf2cbc3b197d21e
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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