HCID 23725567, compound → HCID 23725568, compound

HRID 1881301Notes

Reaction equation

HRID 1881301 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[C:13]3[CH:12]([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[CH2:11][CH2:10][C:9]=3[CH:8]=[CH:7][C:5]=2[N:6]=1>CCCCCC.C(O)C>[CH3:1][C:2]1[S:3][C:4]2[C:13]3[C@@H:12]([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[CH2:11][CH2:10][C:9]=3[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

3

Reactant 1

HCID 23725567HCID 23725567, compound

Product 1

HCID 23725568HCID 23725568, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 21879635Ethanol hexaneSolvent2×

Procedure

Racemic N-[2-(2-methyl-7,8-dihydro-6H-indeno[5,4-d][1,3]thiazol-8-yl)ethyl]acetamide (1.00 g) was fractionated by high performance liquid chromatography (instrument: Prep LC 2000 (manufactured by Nihon Waters K.K.), column: CHIRALPAK AD (50 mmID×500 mL, manufactured by Daicel Chemical Industries, Ltd.), mobile phase: hexane/ethanol=90/10, flow rate: 80 mL/min, column temperature: 30° C., sample concentration: 10 mg/mL (hexane/ethanol=90/10), injection weight: 500 mg×2). A fraction containing an optically active compound having a longer retention time under the above-mentioned high performance liquid chromatography conditions was concentrated to give the title compound (492 mg, 99.9% ee). Enantiomer excess (ee) was measured by high performance liquid chromatography (column: CHIRALPAK AD (4.6 mmID×250 mL, manufactured by Daicel Chemical Industries, Ltd.), mobile phase: hexane/ethanol=90/10, flow rate: 1.0 mL/min, column temperature: 30° C., sample concentration: 0.25 mg/mL (hexane/ethanol=90/10), injection volume: 10 μL).

Workup

  1. additionA fraction containing an optically active compound
  2. concentrationwas concentrated

Sources & evidence

ORD record
ord-170f8b92650643ef89208a991ff8056b
Source dataset
uspto-grants-2012_11
Patent number
US08318784B2

Reaction notes

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