Sodium hydride → (3S)-1,3-bis(tert-Butoxycarbonylamino)-2-pyrrolidone

HRID 2086251Notes

Reaction equation

HRID 2086251 reaction equation
[I-].C[SH2+].[C:4]([NH:11][C@H:12]([C:17]([NH:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:18])[CH2:13][CH2:14]SC)([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[H-].[Na+]>CN(C=O)C>[C:24]([O:23][C:21]([NH:20][N:19]1[CH2:14][CH2:13][C@H:12]([NH:11][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[C:17]1=[O:18])=[O:22])([CH3:27])([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 20720844tert-butyl 2-(Boc-L-methionyl)-1-hydrazine carboxylate methylsulfonium iodide

Product 1

HCID 69545784(3S)-1,3-bis(tert-Butoxycarbonylamino)-2-pyrrolidoneYield 54.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl 2-(Boc-L-methionyl)-1-hydrazine carboxylate methylsulfonium iodide (18 g) in DMF (200 ml) was combined with sodium hydride (3.93 g, in oil) with cooling on ice, and then stirred at room temperature for 3 hours The reaction mixture was combined with ice-water, and extracted with ethyl acetate, and the organic phase was washed with water and brine, dried and concentrated to obtain a residue, which was triturated from isopropyl ether/hexane (1/1) solution, collected by filtration, washed with isopropyl ether/hexane (1/1) solution and dried to obtain the title compound (5.7 g) as a colorless solid.

Workup

  1. temperaturewith cooling on ice
  2. extractionextracted with ethyl acetate
  3. washthe organic phase was washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customto obtain a residue, which
  7. customwas triturated from isopropyl ether/hexane (1/1) solution
  8. filtrationcollected by filtration
  9. washwashed with isopropyl ether/hexane (1/1) solution
  10. customdried

Sources & evidence

ORD record
ord-04ea16e750d44e9192adb86dcb3c6ea2
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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