Sodium Hydroxide → 4-(2-(2-Carboxy-ethyl)-3-{6-[5-(3,3-difluoro-pyrrolidine-1-carbonyl)-biphenyl-3-yloxy]-hexyl}-phenoxy)-butyric acid

HRID 1670133Notes

Reaction equation

HRID 1670133 reaction equation
C(CCC1C(CCCCCCOC2C=C(C3C=CC(F)=C(F)C=3)C=C(C(=O)N(C)C)C=2)=CC=CC=1OCCCC(O)=O)(O)=O.C([O:47][C:48](=[O:94])[CH2:49][CH2:50][CH2:51][O:52][C:53]1[CH:58]=[CH:57][CH:56]=[C:55]([CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][O:65][C:66]2[CH:67]=[C:68]([C:81]3[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=3)[CH:69]=[C:70]([C:72]([N:74]3[CH2:78][CH2:77][C:76]([F:80])([F:79])[CH2:75]3)=[O:73])[CH:71]=2)[C:54]=1[CH2:87][CH2:88][C:89]([O:91]CC)=[O:90])C.[OH-].[Na+]>CCO>[C:89]([CH2:88][CH2:87][C:54]1[C:55]([CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][O:65][C:66]2[CH:67]=[C:68]([C:81]3[CH:82]=[CH:83][CH:84]=[CH:85][CH:86]=3)[CH:69]=[C:70]([C:72]([N:74]3[CH2:78][CH2:77][C:76]([F:80])([F:79])[CH2:75]3)=[O:73])[CH:71]=2)=[CH:56][CH:57]=[CH:58][C:53]=1[O:52][CH2:51][CH2:50][CH2:49][C:48]([OH:94])=[O:47])([OH:91])=[O:90]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67340549HCID 67340549, compoundHCID 67340638HCID 67340638, compound

Product 1

HCID 673380094-(2-(2-Carboxy-ethyl)-3-{6-[5-(3,3-difluoro-pyrrolidine-1-carbonyl)-biphenyl-3-yloxy]-hexyl}-phenoxy)-butyric acidYield 99.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared by the same method as 4-{2-(2-carboxy-ethyl)-3-[6-(5-dimethylcarbamoyl-3′,4′-difluoro-biphenyl-3-yloxy)-hexyl]-phenoxy}-butyric acid starting from 4-[3-{6-[5-(3,3-difluoro-pyrrolidine-1-carbonyl)-biphenyl-3-yloxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (70 mg, 0.101 mmol) and 1.0 N aqueous NaOH (1.01 mL) in EtOH (4 mL) to afford 4-(2-(2-carboxy-ethyl)-3-{6-[5-(3,3-difluoro-pyrrolidine-1-carbonyl)-biphenyl-3-yloxy]-hexyl}-phenoxy)-butyric acid (64 mg, 99%) as a white amorphous solid.

Sources & evidence

ORD record
ord-3f97a4641c3c466f81fab8b58038fd94
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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