proline dl-form → HCID 58392160, compound

HRID 561381Notes

Reaction equation

HRID 561381 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:11][C:12]1([CH3:20])[O:19][C:17](=[O:18])[CH2:16][C:14](=[O:15])[O:13]1.N1CCCC1C(O)=O.[CH3:29][S:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[C:36]2[C:40]=1[NH:39][CH:38]=[CH:37]2>C(#N)C>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]([C:37]1[C:36]2[C:40](=[C:32]([CH2:31][S:30][CH3:29])[CH:33]=[CH:34][CH:35]=2)[NH:39][CH:38]=1)[CH:16]1[C:17](=[O:18])[O:19][C:12]([CH3:20])([CH3:11])[O:13][C:14]1=[O:15]

Participants

6

Reactant 4

HCID 614proline dl-formHCID 134042,4-DichlorobenzaldehydeHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Product 1

HCID 58392160HCID 58392160, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.63 g (9.31 mmol) of 2,4-dichlorobenzaldehyde, 1.34 g (9.31 mmol) of Meldrum's acid and 48.7 mg (0.42 mmol) of D,L-proline were added to a solution of 1.50 g (8.46 mmol) of the compound from Example 8A in 70 ml of acetonitrile. The reaction mixture was stirred at RT overnight. It was concentrated, and the residue was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. 3.99 g (98% of theory) of the title compound were obtained and were reacted without further purification.

Workup

  1. concentrationIt was concentrated
  2. washwashed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5790549c1b264c3eb55ebf4416622083
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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