Water → HCID 54367618, compound

HRID 1870829Notes

Reaction equation

HRID 1870829 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9](=[N:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[S:10][CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:22]I.O>CN(C)C=O>[C:16]([O:15][C:13]([N:12]([CH3:22])[C:9](=[N:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[S:10][CH3:11])=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 5466031,3-DI-Boc-2-methylisothiourea

Product 1

HCID 54367618HCID 54367618, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1,3-Di-(tert-butoxycarbonyl)-2-methyl-isothiourea (Japanese Patent Unexamined Publication No. 2-3661) (2.00 g) was dissolved in N,N-dimethylformamide (20 ml), followed by adding thereto 60% sodium hydride (331 mg), and the resulting mixture was stirred at 50° C. for 2 hours. After the mixture was cooled to 0° C., methyl iodide (1.96 g) was added and the resulting mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate, and the extract solution was washed with water and dried. The solvent was distilled off under reduced pressure and the residue was purified by a silica gel column chromatography to obtain the desired compound (2.07 g).

Workup

  1. additionby adding
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe extract solution was washed with water
  4. customdried
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-33248c8e40ef42f2bbfd4b5decc560e2
Source dataset
uspto-grants-2000_08
Patent number
US06100260

Reaction notes

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