Sodium Hydroxide → 4-[3-{6-[3-Benzo[1,3]dioxol-5-yl-5-(3,3-difluoro-pyrrolidine-1-carbonyl)-phenoxy]-hexyl}-2-(2-carboxy-ethyl)-phenoxy]-butyric acid

HRID 1670132Notes

Reaction equation

HRID 1670132 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:97])[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:71]=[C:70]([C:72]([N:74]3[CH2:78][CH2:77][C:76]([F:80])([F:79])[CH2:75]3)=[O:73])[CH:69]=[C:68]([C:81]3[CH:89]=[CH:88][C:84]4[O:85][CH2:86][O:87][C:83]=4[CH:82]=3)[CH:67]=2)[C:54]=1[CH2:90][CH2:91][C:92]([O:94]CC)=[O:93])C.[OH-].[Na+]>CCO>[O:85]1[C:84]2[CH:88]=[CH:89][C:81]([C:68]3[CH:67]=[C:66]([CH:71]=[C:70]([C:72]([N:74]4[CH2:78][CH2:77][C:76]([F:79])([F:80])[CH2:75]4)=[O:73])[CH:69]=3)[O:65][CH2:64][CH2:63][CH2:62][CH2:61][CH2:60][CH2:59][C:55]3[C:54]([CH2:90][CH2:91][C:92]([OH:94])=[O:93])=[C:53]([CH:58]=[CH:57][CH:56]=3)[O:52][CH2:51][CH2:50][CH2:49][C:48]([OH:97])=[O:47])=[CH:82][C:83]=2[O:87][CH2:86]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67339105HCID 67339105, compoundHCID 67340549HCID 67340549, compound

Product 1

HCID 426441224-[3-{6-[3-Benzo[1,3]dioxol-5-yl-5-(3,3-difluoro-pyrrolidine-1-carbonyl)-phenoxy]-hexyl}-2-(2-carboxy-ethyl)-phenoxy]-butyric acidYield 66%

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-[3-benzo[1,3]dioxol-5-yl-5-(3,3-difluoro-pyrrolidine-1-carbonyl)-phenoxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (120 mg, 0.163 mmol) and 1.0 N aqueous NaOH (1.63 mL) in EtOH (5.7 mL) to afford 4-[3-{6-[3-benzo[1,3]dioxol-5-yl-5-(3,3-difluoro-pyrrolidine-1-carbonyl)-phenoxy]-hexyl}-2-(2-carboxy-ethyl)-phenoxy]-butyric acid (73 mg, 66%) as a white amorphous solid.

Sources & evidence

ORD record
ord-4de14907b998495eb414c22af78e1a73
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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