1-Methylimidazole → (S)-N-[1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethyl]-4-oxo-4-phenylbutanamide

HRID 1046603Notes

Reaction equation

HRID 1046603 reaction equation
[C:1]([CH2:9][CH2:10][C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1C=CN=C1.S(Cl)(Cl)=O.[CH2:24]([C:26]1[N:27]=[C:28]([C@@H:31]([NH2:42])[CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)[S:29][CH:30]=1)[CH3:25]>C(Cl)Cl>[CH2:24]([C:26]1[N:27]=[C:28]([C@@H:31]([NH:42][C:11](=[O:13])[CH2:10][CH2:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)[S:29][CH:30]=1)[CH3:25]

Participants

6

Reactant 4

HCID 13901-MethylimidazoleHCID 24386Thionyl ChlorideHCID 728713-Benzoylpropionic acidHCID 57943187(S)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethanamine

Product 1

HCID 59464671(S)-N-[1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethyl]-4-oxo-4-phenylbutanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Benzoylpropionic acid (0.250 g) is dissolved in CH2Cl2 (5 mL), N-methyl imidazole (0.333 mL) is added and the resulting solution is cooled to 0° C. after which a solution of thionyl chloride (0.320 g) in CH2Cl2 (2 mL) is added dropwise. After 0.5 hours (S)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethanamine, 3, (0.388 g) is added. The reaction is stirred for 18 hours at room temperature and then concentrated in vacuo. The resulting residue is dissolved in EtOAc and washed with 1N HCl and brine. The solution is dried over Na2SO4, filtered, and concentrated and the crude material purified over silica to afford 0.415 g of the desired product.

Workup

  1. additionis added dropwise
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resulting residue is dissolved in EtOAc
  4. washwashed with 1N HCl and brine
  5. dry with materialThe solution is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe crude material purified over silica

Sources & evidence

ORD record
ord-79c4eece71fc4cb595797cf7a79d8185
Source dataset
uspto-grants-2013_10
Patent number
US08569348B2

Reaction notes

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