Isopropanol → (S)-ethyl 3-(4-hydroxyphenyl)-3-(3-methyl-3H-1,2,3-triazol-4-yl)propanoate

HRID 731193Notes

Reaction equation

HRID 731193 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[N:16]([CH3:20])[N:17]=[N:18][CH:19]=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:16]([CH3:20])[N:17]=[N:18][CH:19]=2)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 57835737Ethyl 3-(4-hydroxyphenyl)-3-(3-methyl-3H-1,2,3-triazol-4-yl)propanoate

Product 1

HCID 57835869(S)-ethyl 3-(4-hydroxyphenyl)-3-(3-methyl-3H-1,2,3-triazol-4-yl)propanoateYield 45.4%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Racemic compound 73.5 (3.28 g, 12 mmol) was separated on a semi-preparatory chiral CHIRALCEL OJ-H column (30×250 mm), using 30% i-PrOH in hexane as eluant. Eluant containing the peak with less retention time was concentrated and compound 73.6 (1.5 g, 5.45 mmol) was obtained as off-white solid. The absolute configuration was assigned by analogy to other GPR40 agonist compounds. MS ESI (pos.) m/e 276.1 (M+H).

Workup

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

Sources & evidence

ORD record
ord-46710db3ee254ae7b29974f2ee7bb6c0
Source dataset
uspto-grants-2009_09
Patent number
US07582803B2

Reaction notes

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