Trifluoroacetic acid → HCID 12016525, compound

HRID 411251Notes

Reaction equation

HRID 411251 reaction equation
[CH:1]1([C:4]([C:6]2[CH:33]=[CH:32][C:9]([O:10][CH2:11][CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][N:17]([C:20](=[O:31])[C@@H:21]([NH:23]C(=O)OC(C)(C)C)[CH3:22])[CH2:16][CH2:15]3)=[CH:8][CH:7]=2)=[O:5])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O.C(O)(=O)[C@@H]([C@H](C(O)=O)O)O>ClCCl>[NH2:23][C@@H:21]([CH3:22])[C:20]([N:17]1[CH2:16][CH2:15][N:14]([CH2:13][CH2:12][CH2:11][O:10][C:9]2[CH:8]=[CH:7][C:6]([C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:5])=[CH:33][CH:32]=2)[CH2:19][CH2:18]1)=[O:31]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 444305L-Tartaric acidHCID 12016524HCID 12016524, compound

Product 1

HCID 12016525HCID 12016525, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 1D (3.0 g, 6.5 mmol) in dichloromethane (30 mL) at 0° C. was treated, over a period of 10 minutes, with trifluoroacetic acid (7.5 mL, 97 mmol). The reaction mixture was allowed to warm to room temperature, stirred for 24 hours, and concentrated. The concentrate was dissolved in dichloromethane (300 mL) and the solution was washed sequentially with saturated NaHCO3, water, and brine, dried (MgSO4), filtered, and concentrated. The concentrate was dissolved in methanol (120 mL), treated with L-tartaric acid (1.0 equivalent based on recovered material), stirred for 18 hours at room temperature, and concentrated. The concentrate was dissolved in water (25 mL) and lyophilized to afford the desired product in 83% yield.

Workup

  1. concentrationconcentrated
  2. dissolutionThe concentrate was dissolved in dichloromethane (300 mL)
  3. washthe solution was washed sequentially with saturated NaHCO3, water, and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe concentrate was dissolved in methanol (120 mL)
  8. stirringstirred for 18 hours at room temperature
  9. concentrationconcentrated
  10. dissolutionThe concentrate was dissolved in water (25 mL)

Sources & evidence

ORD record
ord-f525624337fc4a698038f7db32f5164d
Source dataset
uspto-grants-2003_05
Patent number
US06559140B2

Reaction notes

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