Ethanol → HCID 9888604, compound

HRID 1246561Notes

Reaction equation

HRID 1246561 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.C(O)C.[CH3:14][C@:15]1([CH2:18][O:19][C:20]2[CH:21]=[C:22]([C:26]3[C:30]4[S:31][CH:32]=[CH:33][C:29]=4[O:28][N:27]=3)[CH:23]=[CH:24][CH:25]=2)[CH2:17][O:16]1.C(OCC)(=O)C>CO.ClCCl>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][CH2:14][C@@:15]([CH3:17])([OH:16])[CH2:18][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]3[C:30]4[S:31][CH:32]=[CH:33][C:29]=4[O:28][N:27]=3)[CH:21]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 702Ethanol2×HCID 8857Ethyl AcetateHCID 754524-MethoxybenzylamineHCID 58720312HCID 58720312, compound

Product 1

HCID 9888604HCID 9888604, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Add 1 mL of a solution of 4-methoxybenzylamine (0.048 g, 0.00035 mol, Aldrich Chemical Company) and ethanol to 3 mL of a solution of (R)-3-[3-(2-methyloxiranylmethoxy)phenyl]-thieno[2,3-d]isoxazole (example 6, 0.10 g, 0.00035 mol) and ethanol. Shake the reaction mixture under argon at reflux temperature for four hours in a Bohdan apparatus. Cool and concentrate in vacuo to remove the solvent. Purify the residue by flash chromatography (Waters SepPak, silica gel) eluting in step gradient fashion sequentially with 2:1 heptane:ethyl acetate and then with 10:1 dichloromethane:methanol to afford after concentration of the desired fractions the title compound (0.063 g, 42% yield).

Workup

  1. temperatureShake the reaction mixture under argon at reflux temperature for four hours in a Bohdan apparatus
  2. temperatureCool
  3. concentrationconcentrate in vacuo
  4. customto remove the solvent
  5. customPurify the residue by flash chromatography (Waters SepPak, silica gel)
  6. washeluting in step gradient fashion sequentially with 2:1 heptane

Sources & evidence

ORD record
ord-34045a1ffaa349d1a46dc162371da0a9
Source dataset
uspto-grants-2006_10
Patent number
US07125903B1

Reaction notes

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