Formaldehyde → HCID 53746566, compound

HRID 1934571Notes

Reaction equation

HRID 1934571 reaction equation
C=O.[O:3]=[C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]([C:13]([OH:15])=[O:14])[CH2:5]1.N1CCCC[CH2:17]1.[CH3:22][O:23][C:24](=[O:32])[C@H:25]([CH2:30][SH:31])[NH:26][C:27](=[O:29])[CH3:28]>C(O)C>[C:27]([NH:26][C@H:25]([C:24]([O:23][CH3:22])=[O:32])[CH2:30][S:31][CH2:17][CH:5]1[C:4](=[O:3])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]1[C:13]([OH:15])=[O:14])(=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8082PiperidineHCID 998151H-Indene-1-carboxylic acid, 2,3-dihydro-3-oxo-HCID 6542158L-Cysteine, N-acetyl-, methyl ester

Product 1

HCID 53746566HCID 53746566, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After 37% formalin (0.088 ml, 1.08 mmol) was added to a mixture of 3-oxo-1-indanecarboxylic acid (191 mg, 1.08 mmol) and piperidine (92.3 mg, 1.08 mmol), the mixture was stirred at room temperature for 3 hours. The reaction solution was concentrated. Ethanol (3 ml) and N-acetyl-L-cysteine methyl ester (80 mg, 0.45 mmol) were added to the residue. The mixture was heated to reflux for 10 minutes and then concentrated in vacuo. The residue was purified by silica gel column chromatography (100 ml, chloroform:methanol:acetic acid=30:1:0.5) to give Compound (6A) (62 mg, yield: 15.7%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 10 minutes
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (100 ml, chloroform:methanol:acetic acid=30:1:0.5)

Sources & evidence

ORD record
ord-b8c4222dff4f4359b2551b9bcea2f8d1
Source dataset
uspto-grants-2002_05
Patent number
US06384063B1

Reaction notes

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