Triethylamine → HCID 86678890, compound

HRID 1620729Notes

Reaction equation

HRID 1620729 reaction equation
Cl.[CH3:2][N:3]([CH3:11])[C:4](=[O:10])[C@@H:5]1[CH2:9][CH2:8][CH2:7][NH:6]1.C(N(CC)CC)C.S=[C:20]1[CH2:24][S:23][C:22](=[O:25])[NH:21]1>C(O)C>[CH3:2][N:3]([CH3:11])[C:4](=[O:10])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:20]1[CH2:24][S:23][C:22](=[O:25])[N:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15395954-Sulfanylidene-1,3-thiazolidin-2-oneHCID 66702040(S)-N,N-DiMethyl-2-pyrrolidinecarboxaMide HCl

Product 1

HCID 86678890HCID 86678890, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the crude product containing N,N-dimethyl-L-prolinamide hydrochloride obtained in B) (10.5 g) and triethylamine (13.6 g) in ethanol (100 mL) was added 4-thioxothiazolidin-2-one (6.0 g) at room temperature. The reaction mixture was stirred at room temperature for 3 hr, and the solvent was evaporated under reduced pressure. The obtained solid was suspended in THF, and the suspension was filtered through celite pad and silica gel pad. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate) to give the title compound (4.3 g).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. filtrationthe suspension was filtered through celite pad and silica gel pad
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (NH, ethyl acetate)

Sources & evidence

ORD record
ord-229ba7aa35bd4e18a5c8b9d28f2308f0
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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