proline dl-form → HCID 58392486, compound

HRID 561432Notes

Reaction equation

HRID 561432 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[F:10].[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]=[CH:8][C:5]([CH:6]([C:37]2[C:36]3[C:40](=[C:32]([CH2:31][S:30][CH3:29])[CH:33]=[CH:34][CH:35]=3)[NH:39][CH:38]=2)[CH:16]2[C:17](=[O:18])[O:19][C:12]([CH3:20])([CH3:11])[O:13][C:14]2=[O:15])=[CH:4][C:3]=1[F:10]

Participants

6

Reactant 4

HCID 614proline dl-formHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 27249854-Chloro-3-FluorobenzaldehydeHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Product 1

HCID 58392486HCID 58392486, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.34 g (8.46 mmol) of 4-chloro-3-fluorobenzaldehyde, 1.22 g (8.46 mmol) of Meldrum's acid and 0.05 g (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 12 ml of acetonitrile. The reaction mixture was stirred at RT overnight. The precipitated solid was filtered off with suction, washed with acetonitrile and dried under high vacuum. 2.42 g (98% of theory) of the title compound were obtained.

Workup

  1. filtrationThe precipitated solid was filtered off with suction
  2. washwashed with acetonitrile
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-8dd43a86c98c4984b28950b4740a742e
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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