Trifluoroacetic acid → HCID 68748772, compound

HRID 468700Notes

Reaction equation

HRID 468700 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH:5]([NH:12][C:13](=[O:30])[CH:14]([NH:22]C(OC(C)(C)C)=O)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:6][S:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:31])[CH:5]([NH:12][C:13](=[O:30])[CH:14]([NH2:22])[CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:6][S:7][C:8]([CH3:11])([CH3:9])[CH3:10])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68749390HCID 68749390, compound

Product 1

HCID 68748772HCID 68748772, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 23 (6.63 g, 25.0 mmol) in CH2Cl2 (30 mL) was added TFA (30 mL) dropwise at 0° C. The reaction mixture was stirred at room temperature for 1 h, then concentrated. EtOAc (150 mL) was added, washed successively with sat. NaHCO3 (2×20 mL) and brine (20 mL), dried (Na2SO4), and concentrated to give D as a light yellow oil (6.83 g, 99%). 1H NMR (400 MHz, CDCl3) δ 7.94 (br d, 1H), 7.30 (m, 5H), 4.80 (m, 1H), 4.21 (q, 2H), 3.70 (dd, 1H), 3.28 (dd, 1H), 2.99 (m, 2H), 2.74 (dd, 1H), 2.25 (br s, 2H), 1.30 (m, 12H).

Workup

  1. concentrationconcentrated
  2. additionEtOAc (150 mL) was added
  3. washwashed successively with sat. NaHCO3 (2×20 mL) and brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b41e7b0e8fdf45eaad9939128ae74e30
Source dataset
uspto-grants-2014_01
Patent number
US08624052B2

Reaction notes

Loading…