Sodium Bicarbonate → HCID 58677164, compound

HRID 1767044Notes

Reaction equation

HRID 1767044 reaction equation
Br[CH2:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[N:13]=2)[N:8]=[CH:7][C:6]=1Cl)=O.[NH2:18][C:19](=[S:30])[CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].C(=O)(O)[O-].[Na+]>C(O)C>[CH3:16][O:15][C:12]1[N:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[C:3]1[N:18]=[C:19]([CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[S:30][CH:2]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2735653tert-Butyl (3-amino-3-sulfanylidenepropyl)carbamateHCID 21113155HCID 21113155, compound

Product 1

HCID 58677164HCID 58677164, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of bromomethylketone (b) (2.07 g, 9 mmol), 1,1-dimethylethyl (3-amino-3-thioxopropyl)carbamate (1.84 g, 9 mmol) and sodium bicarbonate (0.76 g, 9 mmol) in ethanol (120 mL) was heated to reflux for 1 hour under argon. The mixture was evaporated and the residue partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic extract was washed with brine, dried and evaporated. The residue was chromatographed on silica eluting with a gradient of 0–50% ethyl acetate in dichloromethane affording a yellow solid (0.93 g, 26%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour under argon
  3. customThe mixture was evaporated
  4. customthe residue partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  5. extractionThe organic extract
  6. washwas washed with brine
  7. customdried
  8. customevaporated
  9. customThe residue was chromatographed on silica eluting with a gradient of 0–50% ethyl acetate in dichloromethane affording a yellow solid (0.93 g, 26%)

Sources & evidence

ORD record
ord-86ca6c3531d745408127ab1c47d70046
Source dataset
uspto-grants-2007_06
Patent number
US07232832B2

Reaction notes

Loading…