Trifluoroacetic acid → HCID 67609530, compound

HRID 1965191Notes

Reaction equation

HRID 1965191 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:10]2[N:22]([C:25](=[O:48])[CH:26]([NH:31][C:32](=[O:47])[CH:33]([N:35]([C:37]([O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[O:38])[CH3:36])[CH3:34])[C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:23][CH2:24][CH:9]12)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:40]([O:39][C:37](=[O:38])[N:35]([CH:33]([C:32](=[O:47])[NH:31][CH:26]([C:25]([N:22]1[CH2:23][CH2:24][CH:9]2[NH:8][CH2:12][CH:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:10]12)=[O:48])[C:27]([CH3:28])([CH3:30])[CH3:29])[CH3:34])[CH3:36])[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67606700HCID 67606700, compound

Product 1

HCID 67609530HCID 67609530, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution containing 48 (4.0 g, 5.98 mmol) in DCM (20 mL) was cooled to 0° C. and TFA (10 mL) was added. After 2.5 h, the reaction mixture was concentrated in vacuo and the residue was dissolved in EtOAc. The organic solution was washed successively with aqueous NaHCO3, water, and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 3.3 g of 49 as a beige-colored foam which was used directly in the next reaction. Mass spectrum, m/z [569.1] (M+Na)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe organic solution was washed successively with aqueous NaHCO3, water, and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c5bdb9f1d84947649bf0829664ff53d4
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

Loading…