Methyl 3-Hydroxyphenylacetate → Rac (3-{1-phenyl-2-[3-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-ethoxy}-phenyl)-acetic acid methyl ester

HRID 1452707Notes

Reaction equation

HRID 1452707 reaction equation
C1(C(O)COC2C=CC=C(C(OCC3C=CC(OC)=CC=3)(C(F)(F)F)C(F)(F)F)C=2)C=CC=CC=1.COC(=O)CC1C=CC=C(O)C=1.[CH3:48][O:49][C:50](=[O:93])[CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[C:54]([O:58][CH:59]([C:87]2[CH:92]=[CH:91][CH:90]=[CH:89][CH:88]=2)[CH2:60][O:61][C:62]2[CH:67]=[CH:66][CH:65]=[C:64]([C:68]([O:77]CC3C=CC(OC)=CC=3)([C:73]([F:76])([F:75])[F:74])[C:69]([F:72])([F:71])[F:70])[CH:63]=2)[CH:53]=1>>[CH3:48][O:49][C:50](=[O:93])[CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[C:54]([O:58][CH:59]([C:87]2[CH:92]=[CH:91][CH:90]=[CH:89][CH:88]=2)[CH2:60][O:61][C:62]2[CH:67]=[CH:66][CH:65]=[C:64]([C:68]([OH:77])([C:69]([F:70])([F:71])[F:72])[C:73]([F:75])([F:76])[F:74])[CH:63]=2)[CH:53]=1

Participants

4

Reactant 3

HCID 39129Methyl 3-HydroxyphenylacetateHCID 87605098Rac [3-(1-phenyl-2-{3-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethoxy)-phenyl]-acetic acid methyl esterHCID 87605889Rac 1-phenyl-2-{3-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethanol

Product 1

HCID 11613415Rac (3-{1-phenyl-2-[3-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-ethoxy}-phenyl)-acetic acid methyl ester

Procedure

In analogy to example 9.2, from rac 1-phenyl-2-{3-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethanol (example 9.1) and (3-hydroxy-phenyl)-acetic acid methyl ester was prepared via rac [3-(1-phenyl-2-{3-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethoxy)-phenyl]-acetic acid methyl ester, which was deprotected according to example 13.2, to give rac (3-{1-phenyl-2-[3-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-ethoxy}-phenyl)-acetic acid methyl ester as a colorless oil, MS: 527 (M−H)−.

Sources & evidence

ORD record
ord-a7744faf9e4a4aa59aac1256435aec91
Source dataset
uspto-grants-2009_01
Patent number
US07473705B2

Reaction notes

Loading…