2-(5-Methyl-2-thiophen-2-yloxazol-4-yl)ethyl tosylate → (S)-2-Methyl-3-{4-[2-(5-methyl-2-thiophen-2-yl-oxazol-4-yl)-ethoxy]-phenyl}-2-(4-trifluoromethyl-phenoxy)-propionic Acid

HRID 1393443Notes

Reaction equation

HRID 1393443 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.[CH3:27][C:28]1[O:32][C:31]([C:33]2[S:34][CH:35]=[CH:36][CH:37]=2)=[N:30][C:29]=1[CH2:38][CH2:39]OS(C1C=CC(C)=CC=1)(=O)=O>>[CH3:25][C@:5]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:23])([F:24])[F:22])=[CH:17][CH:16]=1)([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:39][CH2:38][C:29]2[N:30]=[C:31]([C:33]3[S:34][CH:35]=[CH:36][CH:37]=3)[O:32][C:28]=2[CH3:27])=[CH:9][CH:8]=1)[C:4]([OH:3])=[O:26]

Participants

3

Reactant 2

HCID 223400422-(5-Methyl-2-thiophen-2-yloxazol-4-yl)ethyl tosylateHCID 69318029HCID 69318029, compound

Product 1

HCID 60024287(S)-2-Methyl-3-{4-[2-(5-methyl-2-thiophen-2-yl-oxazol-4-yl)-ethoxy]-phenyl}-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-(5-methyl-2-thiophen-2-yl-oxazol-4-yl)-ethyl ester by the procedure described in Example 1.

Sources & evidence

ORD record
ord-4488667a06404eb8baf2f511644708b0
Source dataset
uspto-grants-2008_03
Patent number
US07345070B2

Reaction notes

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