proline dl-form → HCID 58392355, compound

HRID 561377Notes

Reaction equation

HRID 561377 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.[CH3:28][S:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[C:35]2[C:39]=1[NH:38][CH:37]=[CH:36]2>C(#N)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([C:36]2[C:35]3[C:39](=[C:31]([CH2:30][S:29][CH3:28])[CH:32]=[CH:33][CH:34]=3)[NH:38][CH:37]=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 583921877-[(Methylsulfanyl)methyl]-1H-indole

Product 1

HCID 58392355HCID 58392355, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

350 mg (2.49 mmol) of 4-chlorobenzaldehyde, 359 mg (2.49 mmol) of Meldrum's acid and 13.6 mg (0.12 mmol) of D,L-proline were added to a solution of 420 mg (2.40 mmol) of the compound from Example 8A in 20 ml of acetonitrile. The reaction mixture was stirred at RT overnight. It was concentrated, and the crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 650 mg (62% of theory) of the title compound.

Workup

  1. concentrationIt was concentrated
  2. customthe crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record
ord-31ec3d6ecbaf4c1eb991e1393b39c86b
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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