Toluene-4-sulfonic acid 2-(2-cyclohexyl-5-methyloxazol-4-yl)-ethyl ester → (S)-3-{4-[2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methyl-2-(4-trifluoromethyl-phenoxy)-propionic Acid

HRID 1393442Notes

Reaction equation

HRID 1393442 reaction equation
C([O:3][C:4](=[O:26])[C@@:5]([CH3:25])([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)C.[CH:27]1([C:33]2[O:34][C:35]([CH3:51])=[C:36]([CH2:38][CH2:39]OS(C3C=CC(C)=CC=3)(=O)=O)[N:37]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>>[CH:27]1([C:33]2[O:34][C:35]([CH3:51])=[C:36]([CH2:38][CH2:39][O:13][C:10]3[CH:11]=[CH:12][C:7]([CH2:6][C@:5]([CH3:25])([O:14][C:15]4[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][CH:16]=4)[C:4]([OH:3])=[O:26])=[CH:8][CH:9]=3)[N:37]=2)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

3

Reactant 2

HCID 22340021Toluene-4-sulfonic acid 2-(2-cyclohexyl-5-methyloxazol-4-yl)-ethyl esterHCID 69318029HCID 69318029, compound

Product 1

HCID 60024300(S)-3-{4-[2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methyl-2-(4-trifluoromethyl-phenoxy)-propionic Acid

Procedure

The title compound was prepared from (S)-3-(4-hydroxyphenyl)-2-methyl-2-(4-trifluoromethyl-phenoxy)-propionic acid ethyl ester (95% ee; Chiralpak AD separation, 8×27 cm, 10% IPA/heptane, 275 nm) and toluene-4-sulfonic acid 2-(2-cyclohexyl-5-methyl-oxazol-4-yl)-ethyl ester by the procedure described in Example 1.

Sources & evidence

ORD record
ord-c26a95227e904fe4a390cdb614760121
Source dataset
uspto-grants-2008_03
Patent number
US07345070B2

Reaction notes

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