Trifluoroacetic acid → HCID 90110162, compound

HRID 521728Notes

Reaction equation

HRID 521728 reaction equation
FC(F)(F)C(O)=O.[C:8]([NH:16][C:17]1[S:18][CH2:19][C@@H:20]2[CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][C@:21]2([C:33]2[CH:38]=[N:37][CH:36]=[CH:35][N:34]=2)[N:22]=1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClCCl>[N:34]1[CH:35]=[CH:36][N:37]=[CH:38][C:33]=1[C@:21]12[CH2:23][NH:24][CH2:25][C@H:20]1[CH2:19][S:18][C:17]([NH:16][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[N:22]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90121213HCID 90121213, compound

Product 1

HCID 90110162HCID 90110162, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.5 mL) is added to a stirred solution of tert-butyl(4aR,7aR)-2-benzamido-7a-pyrazin-2-yl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate (299 mg, 0.680 mmol) in dichloromethane (6 mL) at room temperature. The reaction is stirred at room temperature for 80 minutes and the solvent is evaporated under reduced pressure. The resulting residue is dissolved in methanol (20 mL) and this solution is loaded onto an ion exchange column and eluted with methanol then with 7 M ammonia/methanol solution. The basic fraction is collected and concentrated under reduced pressure to give the title compound (231 mg, quantitative). ES/MS (m/e): 340 (M+1).

Workup

  1. customthe solvent is evaporated under reduced pressure
  2. dissolutionThe resulting residue is dissolved in methanol (20 mL)
  3. washeluted with methanol
  4. customThe basic fraction is collected
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-63e40e6314df403c8ad1a755f6561305
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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