Isopropanol → HCID 45107306, compound

HRID 1515087Notes

Reaction equation

HRID 1515087 reaction equation
[CH2:1]([O:3][CH:4]([C:9]1[CH:10]=[N:11][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)=[CH:13][CH:14]=1)[CH2:5][C:6]([OH:8])=[O:7])[CH3:2].C(O)(C)C.CCCCCC.C(O)(C)C.FC(F)(F)C(O)=O>CCCCCC>[CH2:1]([O:3][C@H:4]([C:9]1[CH:10]=[N:11][C:12]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:21][CH:22]=2)=[CH:13][CH:14]=1)[CH2:5][C:6]([OH:8])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 22139984HCID 22139984, compoundHCID 45107283HCID 45107283, compound

Product 1

HCID 45107306HCID 45107306, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

3-Ethoxy-3-(6-{[4-(trifluoromethyl)benzyl]oxy}pyridin-3-yl)propionic acid (200 mg) produced in Example 17 (17D) was dissolved in hexane (6 mL) and isopropanol (3 mL) and the resulting solution was subjected to optical resolution by high-performance liquid chromatography using a Chiralpak AD semi-preparative column (2.0 cm×25.0 cm, manufactured by Daicel Chemical Industries, Ltd.) (conditions: flow rate: 20 mL/min, solvent: hexane/isopropanol/trifluoroacetic acid=90/10/0.1 (v/v), detection wavelength: 220 nm). The solvent in the solution having been subjected to optical resolution was distilled off under reduced pressure, and a compound with a retention time of 7 minutes was obtained as (3S)-3-ethoxy-3-(6-{[4-(trifluoromethyl)benzyl]oxy}pyridin-3-yl)propionic acid (a white solid, 45 mg, yield: 23%), and a compound with a retention time of 10 minutes was obtained as (3R)-3-ethoxy-3-(6-{[4-(trifluoromethyl)benzyl]oxy}pyridin-3-yl)propionic acid (a white solid, 47 mg, yield: 24%).

Workup

  1. distillationwas distilled off under reduced pressure

Sources & evidence

ORD record
ord-f7ff91c1ae384365b054d19f339fb5a4
Source dataset
uspto-grants-2012_07
Patent number
US08222281B2

Reaction notes

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