Trifluoroacetic acid → HCID 67398377, compound

HRID 910450Notes

Reaction equation

HRID 910450 reaction equation
C(O[C:6](=O)[N:7]([CH:9]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:12][N:11]([C:20]([N:22]2[CH2:27][CH2:26][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][CH2:23]2)=[O:21])[CH2:10]1)C)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:31][S:28]([N:25]1[CH2:24][CH2:23][N:22]([C:20]([N:11]2[CH2:12][CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:9]([NH:7][CH3:6])[CH2:10]2)=[O:21])[CH2:27][CH2:26]1)(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67025895HCID 67025895, compound

Product 1

HCID 67398377HCID 67398377, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [(3RS,4SR)-1-(4-Methanesulfonyl-piperazine-1-carbonyl)-4-phenyl-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester (640 mg, 1.37 mmol) in CH2Cl2 (10 ml) was added TFA (2 ml). The reaction mixture was stirred at RT for 2 hours, aqueous NaHCO3 was added until pH=8 and the product was extracted with CH2Cl2. The combined organic phase were dried over Na2SO4. Concentration under vacuo gave 500 mg (99%) of the title product as a white solid. ES-MS m/e: 367.1 (M+H+).

Workup

  1. extractionthe product was extracted with CH2Cl2
  2. dry with materialThe combined organic phase were dried over Na2SO4
  3. concentrationConcentration under vacuo

Sources & evidence

ORD record
ord-d89c1e9213ae4898b4a37d5a230cacf5
Source dataset
uspto-grants-2011_09
Patent number
US08022099B2

Reaction notes

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