proline dl-form → HCID 59293936, compound

HRID 561376Notes

Reaction equation

HRID 561376 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH3:13][C:14]1([CH3:22])[O:21][C:19](=[O:20])[CH2:18][C:16](=[O:17])[O:15]1.N1CCCC1C(O)=O.[CH3:31][S:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[C:38]2[C:42]=1[NH:41][CH:40]=[CH:39]2>C(#N)C>[CH3:13][C:14]1([CH3:22])[O:21][C:19](=[O:20])[CH:18]([CH:7]([C:39]2[C:38]3[C:42](=[C:34]([CH2:33][S:32][CH3:31])[CH:35]=[CH:36][CH:37]=3)[NH:41][CH:40]=2)[C:6]2[CH:9]=[CH:10][C:3]([C:2]([F:12])([F:11])[F:1])=[CH:4][CH:5]=2)[C:16](=[O:17])[O:15]1

Participants

6

Reactant 4

HCID 614proline dl-formHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 679964-(Trifluoromethyl)benzaldehydeHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Product 1

HCID 59293936HCID 59293936, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

268 mg (1.54 mmol) of 4-(trifluoromethyl)benzaldehyde, 222 mg (1.54 mmol) of Meldrum's acid and 8.4 mg (0.07 mmol) of D,L-proline were added to a solution of 260 mg (1.47 mmol) of the compound from Example 8A in 12 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 504 mg (72% 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-45c1693bc21b46649e56642ad6b80e09
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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