Benzyl mercaptan → HCID 22053951, compound

HRID 1830140Notes

Reaction equation

HRID 1830140 reaction equation
[CH2:1](S)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(S[CH2:17][CH:18]([CH2:22][C:23]([N:25]1[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]1)=[O:24])[C:19]([OH:21])=[O:20])C1C=CC=CC=1.O[O:33][S:34]([O-:36])=O.[K+]>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[CH3:31][N:28]1[CH2:27][CH2:26][N:25]([C:23](=[O:24])[CH2:22][CH:18]([CH2:17][S:34]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)(=[O:36])=[O:33])[C:19]([OH:21])=[O:20])[CH2:30][CH2:29]1

Participants

7

Reactant 3

HCID 7509Benzyl mercaptanHCID 22053994HCID 22053994, compoundHCID 23707502Potassium hydroxy sulfite2×

Product 1

HCID 22053951HCID 22053951, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirring mixture of itacconic anhydride 1.1209 g, 10 mmol) in 10 ml of methylene chloride at 0° C. was added drop wise methyl piperizine (1.0 g, 10 mmol). The reaction was stirred at room temperature for 1 hour and the solvent was removed under reduced pressure to give compound 2-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-acrylic acid. The residue was dissolved in 10 ml of DMF, then benzyl mercaptan (1.17 g, 10.0 mmol) and DMAP (122 mg, 1 mmol) were added and heated to 50–60° C. until reaction turned clear then the reaction was stirred at room temperature for overnight. Another 0.59 ml of benzyl mercapton (5 mmol) was added and the reaction was stirred overnight at room temperature. The mixture containing compound 2-benzylsulfanylmethyl-4-(4-methyl-piperazin-1-yl)-4-oxo-butyric acid was cooled to 0° C. and oxone® (6.1378 g, 10 mmol) in 20 ml of water was added and stirred for overnight at room temperature. More oxone® was added and the reaction was stirred at room temperature for 2 hours. The reaction was filtered and the product was in the aqueous phase and was purified on HPLC to give 0.2477 gram of pure 4-(4-methyl-piperazin-1-yl)-4-oxo-2-benzylsulfonylmethyl-butyric acid; LCMS retention time: 1.72 minutes; M+1 (369.3).

Workup

  1. temperatureheated to 50–60° C. until reaction
  2. additionAnother 0.59 ml of benzyl mercapton (5 mmol) was added
  3. stirringthe reaction was stirred overnight at room temperature
  4. temperaturewas cooled to 0° C.
  5. stirringstirred for overnight at room temperature
  6. stirringthe reaction was stirred at room temperature for 2 hours
  7. filtrationThe reaction was filtered
  8. customwas purified on HPLC

Sources & evidence

ORD record
ord-d1406a81582d4d738f38daa7abfb299f
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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