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proline dl-form → 5-[(4-Chlorophenyl){7-[(ethylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 561378
Notes
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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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 583925285-[(4-Chlorophenyl){7-[(ethylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08063234B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes