Trifluoroacetic acid → HCID 11223031, compound

HRID 604579Notes

Reaction equation

HRID 604579 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][C:10]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:14]([C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[N:13]=[C:12]([NH:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[S:11]1)(C)(C)C.[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38]>ClCCl>[F:35][C:36]([F:41])([F:40])[C:37]([O-:39])=[O:38].[NH2:7][CH2:8][CH2:9][C:10]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[S:11][C:12]([NH:21][C:22](=[O:27])[C:23]([CH3:24])([CH3:25])[CH3:26])=[N:13][N:14]1[C:15](=[O:20])[C:16]([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67039212HCID 67039212, compound

Product 2

HCID 84468TrifluoroacetateHCID 11223031HCID 11223031, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{2-[3-(2,2-Dimethylpropionyl)-5-(2,2-dimethylpropionylamino)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl]ethyl}carbamic acid tert-butyl ester (274 mg, 0.557 mmol) obtained in Step 2 mentioned above was dissolved in dichloromethane (10 mL). To the resulting solution was added trifluoroacetic acid (1.0 mL), and the mixture was stirred at room temperature for 3 hours, and then concentrated under reduced pressure. To the residue was added diisopropyl ether, and the mixture was stirred for 3 hours. The deposited white solid was collected by filtration to give trifluoroacetate of N-[5-(2-aminoethyl)-4-(2,2-dimethylpropionyl)-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl]-2,2-dimethylpropanamide (252 mg, 90%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue was added diisopropyl ether
  3. stirringthe mixture was stirred for 3 hours
  4. filtrationThe deposited white solid was collected by filtration

Sources & evidence

ORD record
ord-79ffebe7ae894b9d86b31228307c1038
Source dataset
uspto-grants-2011_03
Patent number
US07910611B2

Reaction notes

Loading…