Hydrochloric Acid → HCID 67039194, compound

HRID 604584Notes

Reaction equation

HRID 604584 reaction equation
[CH3:1][C:2]([CH3:37])([CH3:36])[C:3]([N:5]1[N:9]=[C:8]([NH:10][C:11](=[O:20])[CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[S:7][C:6]1([CH2:27][CH2:28][CH2:29][C:30]([NH:32][CH2:33][CH2:34][OH:35])=[O:31])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:4].N1C=CC=CC=1.[Si:44](Cl)([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45].Cl>O.ClCCl>[O:35]([CH2:34][CH2:33][NH:32][C:30](=[O:31])[CH2:29][CH2:28][CH2:27][C:6]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:5]([C:3](=[O:4])[C:2]([CH3:36])([CH3:1])[CH3:37])[N:9]=[C:8]([NH:10][C:11](=[O:20])[CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[S:7]1)[Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 67039644HCID 67039644, compound

Product 1

HCID 67039194HCID 67039194, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 4-[3-(2,2-dimethylpropionyl)-2-phenyl-5-(2-phenylpropionylamino)-2,3-dihydro-1,3,4-thiadiazol-2-yl]-N-(2-hydroxyethyl)butanamide (1.21 g, 2.31 mmol) obtained in Step 4 mentioned above was added dichloromethane (20 mL), and the mixture was stirred at 0° C. Then, to the mixture were added pyridine (0.470 mL, 5.77 mmol) and tert-butyldimethylsilyl chloride (869 mg, 5.77 mmol), and the mixture was stirred at room temperature for 3 hours. To the mixture were added 1 mol/L hydrochloric acid (20 mL) and water (30 mL), and the mixture was extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To the resulting residue was added diisopropyl ether, and the deposited white solid was collected by filtration. The resulting solid was washed with water and diisopropyl ether, and dried under reduced pressure to give N-[2-(tert-butyldimethylsiloxy)ethyl]-4-[3-(2,2-dimethylpropionyl)-2-phenyl-5-(2-phenylpropionylamino)-2,3-dihydro-1,3,4-thiadiazol-2-yl]butanamide (1.25 g, 85%).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the resulting residue was added diisopropyl ether
  7. filtrationthe deposited white solid was collected by filtration
  8. washThe resulting solid was washed with water and diisopropyl ether
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-c56a1b19851540c98b86e593a92a296d
Source dataset
uspto-grants-2011_03
Patent number
US07910611B2

Reaction notes

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