Trifluoroacetic acid → HCID 67539670, compound

HRID 2066999Notes

Reaction equation

HRID 2066999 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])=[C:16]([Cl:21])[CH:15]=2)[CH2:12][N:11]([C:22](=[O:31])[C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[CH2:10]1)C)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:21][C:16]1[CH:15]=[C:14]([CH:13]2[CH:9]([NH:7][CH3:6])[CH2:10][N:11]([C:22]([C:23]3[CH:24]=[CH:25][C:26]([C:29]#[N:30])=[CH:27][CH:28]=3)=[O:31])[CH2:12]2)[CH:19]=[CH:18][C:17]=1[Cl:20]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67217944HCID 67217944, compound

Product 1

HCID 67539670HCID 67539670, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [(3RS,4SR)-1-(4-cyano-benzoyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester (414 mg, 0.87 mmol) in CH2Cl2 (8 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 302 mg (92%) of the title product as a colorless oil. ES-MS m/e: 374.1 (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-56c324e843b44fda8081ff46b02dd6d3
Source dataset
uspto-grants-2012_10
Patent number
US08293770B2

Reaction notes

Loading…