Sodium → 4-t-Butoxycarbonyl-3-[2-(methylthio)ethyl]piperazinone

HRID 1413718Notes

Reaction equation

HRID 1413718 reaction equation
[Na].[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][N:12](CC2C=CC=CC=2)[C:11](=[O:22])[CH:10]1[CH2:23][CH2:24][S:25][CH3:26])=[O:8])([CH3:5])([CH3:4])[CH3:3]>COCCOCCOC.N>[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][NH:12][C:11](=[O:22])[CH:10]1[CH2:23][CH2:24][S:25][CH3:26])=[O:8])([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 5360545SodiumHCID 233196654-t-Butoxycarbonyl-3-[2-(methylthio)ethyl)-1-(phenylmethyl)piperazinone

Product 1

HCID 233196714-t-Butoxycarbonyl-3-[2-(methylthio)ethyl]piperazinone

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolvent2×HCID 8150DiglymeSolvent

Procedure

Sodium metal (1.3 g., 0.057 mole) is added to a stirred solution of 4-t-butoxycarbonyl-3-[2-(methylthio)ethyl]-1-(phenylmethyl)-2-piperazinone (XVI, Example 42, 3.71 g., 0.01 mole) in diglyme (100 ml.) and ammonia (500 ml.) at -60°. The solution is allowed to reflux for 2 hours, the ammonia is allowed to evaporate and the diglyme is removed at 20°-25° under reduced pressure. The residue is partitioned between diethylether and water. Evaporation of the diethylether gives the title compound.

Workup

  1. temperatureto reflux for 2 hours
  2. customto evaporate
  3. customthe diglyme is removed at 20°-25° under reduced pressure
  4. customThe residue is partitioned between diethylether and water
  5. customEvaporation of the diethylether

Sources & evidence

ORD record
ord-1f4b894935ef43ee9f4c4a391f92a241
Source dataset
uspto-grants-1981_02
Patent number
US04251438

Reaction notes

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