Sodium Hydroxide → HCID 178503955, compound

HRID 1636225Notes

Reaction equation

HRID 1636225 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9](=[NH:12])[S:10][CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[CH2:15]([O:22][C:23](ON1C(=O)CCC1=O)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>ClCCl>[CH2:15]([O:22][C:23]([NH:12][C:9](=[N:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[S:10][CH3:11])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 83172Benzyl succinimido carbonateHCID 137319820tert-butyl N-[(methylsulfanyl)methanimidoyl]carbamate

Product 1

HCID 178503955HCID 178503955, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-(tert-butyloxycarbonyl)-S-methylisothiourea (2 g) was dissolved in dichloromethane (20 ml). To the solution, a 4N sodium hydroxide solution (2 ml) was added with stirring. The reaction mixture was placed in an ice bath; N-(benzyloxy-carbonyloxy)-succinimid (2.62 g) in dichloromethane (20 ml) was added dropwise together with a 2N sodium hydroxide solution to keep the pH around 11. After addition was complete, the reaction mixture was stirred overnight at room temperature. The dichloromethane layer was separated, and the aqueous layer was washed twice with dichloromethane. The combined organic layers were washed with water and dried over sodium sulfate, filtered and evaporated in vacuo. The residue was purified by chromatography on silica (eluent: heptane/ethyl acetate=3/2 v/v %) to yield N-(benzyloxy-carbonyl)-N'-(tert-butyloxycarbonyl)-S-methylisothiourea (3.15 g).

Workup

  1. customThe reaction mixture was placed in an ice bath
  2. additionAfter addition
  3. stirringthe reaction mixture was stirred overnight at room temperature
  4. customThe dichloromethane layer was separated
  5. washthe aqueous layer was washed twice with dichloromethane
  6. washThe combined organic layers were washed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue was purified by chromatography on silica (eluent: heptane/ethyl acetate=3/2 v/v %)

Sources & evidence

ORD record
ord-28174487b83447518f3f1b022dfba1e2
Source dataset
uspto-grants-2000_03
Patent number
US06034067

Reaction notes

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