Isopropanol → (S)-ethyl 3-(4-hydroxyphenyl)-3-(oxazol-5-yl)propanoate

HRID 731204Notes

Reaction equation

HRID 731204 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[O:19][CH:18]=[N:17][CH:16]=2)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.CC(O)C>CCCCCC>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:15]2[O:19][CH:18]=[N:17][CH:16]=2)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 57835798Ethyl 3-(4-hydroxyphenyl)-3-(oxazol-5-yl)propanoate

Product 1

HCID 57835908(S)-ethyl 3-(4-hydroxyphenyl)-3-(oxazol-5-yl)propanoateYield 47.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Racemic compound 75.4 (1.3 g, 5 mmol) was separated on a semi-preparatory chiral CHIRALCEL OJ-H column (30×250 mm), using 20% i-PrOH in hexane as eluant. Eluant containing the peak with greater retention time was concentrated and compound 75.5 (620 mg, 2.38 mmol) was obtained as off-white solid. The absolute configuration was assigned by analogy to other GPR40 agonist compounds. MS ESI (pos.) m/e 262.1 (M+H).

Workup

  1. additionEluant containing the peak with greater retention time
  2. concentrationwas concentrated

Sources & evidence

ORD record
ord-427b8859cbb144aebdb26a143f1bbbcb
Source dataset
uspto-grants-2009_09
Patent number
US07582803B2

Reaction notes

Loading…