Methyl iodide → tert-butyl 2-(Boc-L-methionyl)-1-hydrazine carboxylate methylsulfonium iodide

HRID 2086250Notes

Reaction equation

HRID 2086250 reaction equation
[C:1]([NH:8][C@H:9]([C:14]([NH:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:15])[CH2:10][CH2:11][S:12][CH3:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C[I:26]>CC(C)=O>[I-:26].[CH3:11][SH2+:12].[C:1]([NH:8][C@H:9]([C:14]([NH:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:15])[CH2:10][CH2:11][S:12][CH3:13])([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 20720845tert-butyl 2-(Boc-L-methionyl)-1-hydrazine carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of the resultant tert-butyl 2-(Boc-L-methionyl)-1-hydrazine carboxylate in acetone (20 ml) was combined with methyl iodide (17 ml, 240 mmol) and stirred at room temperature overnight. The reaction mixture was concentrated, and the resultant residue was triturated from ether, collected by filtration, washed with ether and dried to obtain tert-butyl 2-(Boc-L-methionyl)-1-hydrazine carboxylate methylsulfonium iodide (19.14 g) as a colorless solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe resultant residue was triturated from ether
  3. filtrationcollected by filtration
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-6fb8d05331a14c06b9a489fd840de79d
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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