Isopropanol → (S)-ethyl 3-(4-hydroxyphenyl)-3-(1-methyl-1H-imidazol-5-yl)propanoate

HRID 731198Notes

Reaction equation

HRID 731198 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[N:19]([CH3:20])[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[N:19]([CH3:20])[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 57835914Ethyl 3-(4-hydroxyphenyl)-3-(1-methyl-1H-imidazol-5-yl)propanoate

Product 1

HCID 57835788(S)-ethyl 3-(4-hydroxyphenyl)-3-(1-methyl-1H-imidazol-5-yl)propanoateYield 44%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Racemic compound 74.4 (680 mg, 2.5 mmol) was separated on a semi-preparatory chiral CHIRALCEL OJ-H column (30×250 mm), using 15% i-PrOH in hexane as eluant. Eluant containing the peak with less retention time was concentrated and compound 74.5 (300 mg, 1.1 mmol) was obtained as off-white solid. The absolute configuration was assigned by analogy to other GPR40 agonist compounds. MS ESI (pos.) m/e 275.2 (M+H).

Workup

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

Sources & evidence

ORD record
ord-e30f7cd0c4ea4d0cb7f24a77106706c5
Source dataset
uspto-grants-2009_09
Patent number
US07582803B2

Reaction notes

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