proline dl-form → HCID 58392528, compound

HRID 561378Notes

Reaction equation

HRID 561378 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C:11]1([CH3:19])[O:18][C:16](=[O:17])[CH2:15][C:13](=[O:14])[O:12]1.N1CCCC1C(O)=O.[CH2:28]([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)[CH3:29]>C(#N)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([C:37]2[C:36]3[C:40](=[C:32]([CH2:31][S:30][CH2:28][CH3:29])[CH:33]=[CH:34][CH:35]=3)[NH:39][CH:38]=2)[CH:15]2[C:16](=[O:17])[O:18][C:11]([CH3:19])([CH3:10])[O:12][C:13]2=[O:14])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 614proline dl-formHCID 77264-ChlorobenzaldehydeHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 583922897-[(Ethylsulfanyl)methyl]-1H-indole

Product 1

HCID 58392528HCID 58392528, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.00 g (7.14 mmol) of 4-chlorobenzaldehyde, 1.03 g (7.14 mmol) of Meldrum's acid and 39.1 mg (0.34 mmol) of D,L-proline were added to a solution of 1.30 g (6.80 mmol) of the compound from Example 10A in 57 ml of acetonitrile. The reaction mixture was stirred at RT overnight. It was concentrated, and the crude product was stirred in diethyl ether and filtered, and the precipitate was dried under high vacuum to result in 1.38 g (44% of theory) of the title compound.

Workup

  1. concentrationIt was concentrated
  2. stirringthe crude product was stirred in diethyl ether
  3. filtrationfiltered
  4. customthe precipitate was dried under high vacuum

Sources & evidence

ORD record
ord-dc11dcd3f9ad45549bf8dbc4111a09a8
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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