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

HRID 1670134Notes

Reaction equation

HRID 1670134 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:93])[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]3[CH:76]=[CH:75][S:74][CH:73]=3)[CH:69]=[C:68]([C:77]([N:79]3[CH2:83][CH2:82][C:81]([F:85])([F:84])[CH2:80]3)=[O:78])[CH:67]=2)[C:54]=1[CH2:86][CH2:87][C:88]([O:90]CC)=[O:89])C.[OH-].[Na+]>CCO>[C:88]([CH2:87][CH2:86][C:54]1[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]3[CH:76]=[CH:75][S:74][CH:73]=3)[CH:69]=[C:68]([C:77]([N:79]3[CH2:83][CH2:82][C:81]([F:84])([F:85])[CH2:80]3)=[O:78])[CH:67]=2)=[CH:56][CH:57]=[CH:58][C:53]=1[O:52][CH2:51][CH2:50][CH2:49][C:48]([OH:93])=[O:47])([OH:90])=[O:89]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67339942HCID 67339942, compoundHCID 67340549HCID 67340549, compound

Product 1

HCID 673383564-(2-(2-Carboxy-ethyl)-3-{6-[3-(3,3-difluoro-pyrrolidine-1-carbonyl)-5-thiophen-3-yl-phenoxy]-hexyl}-phenoxy)-butyric acidYield 91.4%

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-[3-(3,3-difluoro-pyrrolidine-1-carbonyl)-5-thiophen-3-yl-phenoxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (71 mg, 0.11 mmol) and 1.0 N aqueous NaOH (1.1 mL) in EtOH (5 mL) to afford 4-(2-(2-carboxy-ethyl)-3-{6-[3-(3,3-difluoro-pyrrolidine-1-carbonyl)-5-thiophen-3-yl-phenoxy]-hexyl}-phenoxy)-butyric acid (64.7 mg, 91%) as a white amorphous solid.

Sources & evidence

ORD record
ord-62ae3897a42249938139375314dd2046
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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