proline dl-form → HCID 58392087, compound

HRID 561384Notes

Reaction equation

HRID 561384 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=O.[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:11]([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:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[C:16](=[O:17])[O:15]1

Participants

6

Reactant 4

HCID 614proline dl-formHCID 62012-NaphthalenecarboxaldehydeHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Product 1

HCID 58392087HCID 58392087, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

694 mg (4.44 mmol) of naphthalene-2-carbaldehyde, 640 mg (4.44 mmol) of Meldrum's acid and 24 mg (0.21 mmol) of D,L-proline were added to a solution of 750 mg (4.23 mmol) of the compound from Example 8A in 35 ml of acetonitrile. The reaction mixture was stirred at RT overnight. Then a further 35 ml of acetonitrile were added, and the mixture was stirred at RT for two days. It was concentrated, the residue was stirred in water, and the precipitate was filtered off with suction and dried in vacuo at 50° C. for 1 h. The crude product was stirred in acetonitrile, and the precipitate was filtered off with suction and dried under high vacuum to result in 882 mg (45% of theory) of the title compound which were reacted without further purification.

Workup

  1. stirringthe mixture was stirred at RT for two days
  2. concentrationIt was concentrated
  3. stirringthe residue was stirred in water
  4. filtrationthe precipitate was filtered off with suction
  5. customdried in vacuo at 50° C. for 1 h
  6. stirringThe crude product was stirred in acetonitrile
  7. filtrationthe precipitate was filtered off with suction
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-5aeab0f5795d4771b49c96dad559d854
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

Loading…