Sodium Hydroxide → 4-(2-(2-Carboxy-ethyl)-3-{6-[5-(2-difluoromethoxy-benzylcarbamoyl)-2'-fluoro-bi phenyl-3-yloxy]-hexyl}-phenoxy)-butyric acid

HRID 1670138Notes

Reaction equation

HRID 1670138 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:100])[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:86]3[CH:91]=[CH:90][CH:89]=[CH:88][C:87]=3[F:92])[CH:69]=[C:70]([C:72](=[O:85])[NH:73][CH2:74][C:75]3[CH:80]=[CH:79][CH:78]=[CH:77][C:76]=3[O:81][CH:82]([F:84])[F:83])[CH:71]=2)[C:54]=1[CH2:93][CH2:94][C:95]([O:97]CC)=[O:96])C.[OH-].[Na+]>C1COCC1.CCO>[C:95]([CH2:94][CH2:93][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:86]3[CH:91]=[CH:90][CH:89]=[CH:88][C:87]=3[F:92])[CH:69]=[C:70]([C:72](=[O:85])[NH:73][CH2:74][C:75]3[CH:80]=[CH:79][CH:78]=[CH:77][C:76]=3[O:81][CH:82]([F:83])[F:84])[CH:71]=2)=[CH:56][CH:57]=[CH:58][C:53]=1[O:52][CH2:51][CH2:50][CH2:49][C:48]([OH:100])=[O:47])([OH:97])=[O:96]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 673379514-[3-{6-[5-(2-Difluoromethoxy-benzylcarbamoyl)-2'-fluoro-biphenyl-3-yloxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl esterHCID 67340549HCID 67340549, compound

Product 1

HCID 673383494-(2-(2-Carboxy-ethyl)-3-{6-[5-(2-difluoromethoxy-benzylcarbamoyl)-2'-fluoro-bi phenyl-3-yloxy]-hexyl}-phenoxy)-butyric acidYield 91%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

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-(2-difluoromethoxy-benzylcarbamoyl)-2′-fluoro-bi phenyl-3-yloxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (100 mg, 0.128 mmol) and 1.0 N aqueous NaOH (5 mL) in THF (5 mL) and EtOH (5 mL) to afford 4-(2-(2-carboxy-ethyl)-3-{6-[5-(2-difluoromethoxy-benzylcarbamoyl)-2′-fluoro-bi phenyl-3-yloxy]-hexyl}-phenoxy)-butyric acid (84 mg, 91%) as a white amorphous solid.

Sources & evidence

ORD record
ord-3e8f3c41e80d41ea9c0f5fda2652d6fe
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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