Water → HCID 178504138, compound

HRID 604590Notes

Reaction equation

HRID 604590 reaction equation
ClC[S:3]([NH:6][CH2:7][C:8]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[S:12][C:11]([NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[N:10][N:9]1[C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:5])=[O:4].[SH:32][CH2:33][CH2:34][NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39].[C:43](=O)([O-])O.[Na+].O>CN(C=O)C>[C:38]([O:37][C:36](=[O:42])[NH:35][CH2:34][CH2:33][SH:32]([S:3](=[O:5])(=[O:4])[NH:6][CH2:7][C:8]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:9]([C:20](=[O:25])[C:21]([CH3:23])([CH3:22])[CH3:24])[N:10]=[C:11]([NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:16])[CH3:17])[S:12]1)[CH3:43])([CH3:39])([CH3:41])[CH3:40]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 3017761N-(tert-butoxycarbonyl)-2-aminoethanethiolHCID 67039236HCID 67039236, compound

Product 1

HCID 178504138HCID 178504138, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

N-[5-Chloromethanesulfonylaminomethyl-4-(2,2-dimethylpropionyl)-5-phenyl-4,5-dihydro[1,3,4]thiadiazol-2-yl]-2,2-dimethylpropionamide (3.818 g, 7.807 mmol) obtained in Step 1 mentioned above was dissolved in DMF (70 mL), and tert-butyl N-(2-mercaptoethyl)carbamate (13.3 mL, 78.1 mmol) and saturated aqueous sodium hydrogencarbonate (15 mL) were added, then the mixture was stirred at 70° C. for 5.5 hours. After cooling, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=9/1→7/3), and then triturated with diisopropyl ether to give [2-({[3-(2,2-dimethylpropionyl)-5-(2,2-dimethyl-propionylamino)-2-phenyl-2,3-dihydro[1,3,4]thiadiazol-2-ylmethyl]sulfamoyl}-methylsulfanyl)ethyl]carbamic acid tert-butyl ester (1.926 g, 39%).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=9/1→7/3)
  7. customtriturated with diisopropyl ether

Sources & evidence

ORD record
ord-c0f9f6e763bc424d9509ce86cef677a6
Source dataset
uspto-grants-2011_03
Patent number
US07910611B2

Reaction notes

Loading…