Water → HCID 18703842, compound

HRID 2288028Notes

Reaction equation

HRID 2288028 reaction equation
Cl.[CH:2]1([C:5]([CH:7]([N:15]2[CH2:20][CH2:19][CH:18]([SH:21])[CH2:17][CH2:16]2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])=[O:6])[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:29](Cl)(=[O:33])[CH2:30][CH2:31][CH3:32].O>ClCCl>[C:29]([S:21][CH:18]1[CH2:17][CH2:16][N:15]([CH:7]([C:5]([CH:2]2[CH2:4][CH2:3]2)=[O:6])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])[CH2:20][CH2:19]1)(=[O:33])[CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 23000863HCID 23000863, compound

Product 1

HCID 18703842HCID 18703842, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 5 ml of dichloromethane, 0.50 g (1.5 mmol) of 1-(α-cyclopropylcarbonyl-2-fluorobenzyl)-4-mercaptopiperidine hydrochloride were dissolved, followed by the addition of 0.3 g (3 mmol) of triethylamine. To the resulting mixture, a solution of 0.16 g (1.5 mmol) of butyryl chloride in 1 ml of dichloromethane was added dropwise under ice cooling and the resulting mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture, followed by extraction with dichloromethane. The extract was dried over anhydrous sodium sulfate. The solvent was concentrated by evaporation under reduced pressure and the residue was subjected to chromatography on a silica gel column (eluting solvent: toluene/ethyl acetate=30/1), whereby 0.32 g (yield: 58%) of the title compound was obtained as white crystals.

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationThe solvent was concentrated by evaporation under reduced pressure
  4. washthe residue was subjected to chromatography on a silica gel column (eluting solvent: toluene/ethyl acetate=30/1)

Sources & evidence

ORD record
ord-abf8a52d11fc40cfbc9cce091469e207
Source dataset
uspto-grants-2000_07
Patent number
US06087379

Reaction notes

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