Trifluoroacetic acid → HCID 67539773, compound

HRID 2066997Notes

Reaction equation

HRID 2066997 reaction equation
C(O[C:6](=O)[N:7]([CH:9]1[CH:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:12][N:11]([C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:10]1)C)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([CH:13]2[CH:9]([NH:7][CH3:6])[CH2:10][N:11]([C:21]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:28])[CH2:12]2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67217495HCID 67217495, compound

Product 1

HCID 67539773HCID 67539773, compoundYield 107%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [(3RS,4SR)-1-benzoyl-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester (80 mg, 0.19 mmol) in CH2Cl2 (1 ml) was added TFA (0.2 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 64 mg (95%) of the title product as a colorless oil. ES-MS m/e: 315.1 (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-4978490c0a6a40568e1702894052fb72
Source dataset
uspto-grants-2012_10
Patent number
US08293770B2

Reaction notes

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