Trifluoroacetic acid → HCID 46893526, compound

HRID 1879624Notes

Reaction equation

HRID 1879624 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:42]([F:45])([F:44])[F:43])[CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[N:8]=[C:7]2[CH:12]([C:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=1)[CH:13]([C:17]1[CH:34]=[CH:33][C:20]([C:21]([NH:23][CH2:24][CH2:25][C:26]([O:28]C(C)(C)C)=[O:27])=[O:22])=[CH:19][CH:18]=1)[CH2:14][CH2:15][CH3:16].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:42]([F:44])([F:43])[F:45])[CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[N:8]=[C:7]2[CH:12]([C:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=1)[CH:13]([C:17]1[CH:34]=[CH:33][C:20]([C:21]([NH:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[O:22])=[CH:19][CH:18]=1)[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71059042HCID 71059042, compound

Product 1

HCID 46893526HCID 46893526, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the slower-eluting enantiomer of the product from Step B (4.6 mg, 0.0069 mmol) in DCM (1 mL) was added TFA (1 mL, 13 mmol), and the solution was stirred for 30 minutes at RT. The solution was concentrated, then the residue was purified by reverse phase HPLC eluting with acetonitrile/water+0.1% TFA. Following lyophilization, this afforded the enantiopure title compound as a white solid. 1H NMR (500 MHz, CD3OD): δ 7.92 (s, 1H); 7.62 (d, J=8.5 Hz, 2H); 7.53 (d, J=8.3 Hz, 2H); 7.43 (s, 1H); 7.36 (d, J=8.2 Hz, 2H); 7.33 (d, J=8.5 Hz, 2H); 4.78 (d, 3=11.5 Hz, 1H); 4.26 (s, 3H); 3.72 (td, J=11.4, 3.2 Hz, 1H); 3.52 (t, J=6.9 Hz, 2H); 2.55 (t, J=6.9 Hz, 2H); 1.68-1.57 (m, 1H); 1.50-1.43 (m, 1H); 1.05-0.97 (m, 2H); 0.73 (t, J=7.3 Hz, 3H); LC2 1.31 min. (M+H)+ 606.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was purified by reverse phase HPLC
  3. washeluting with acetonitrile/water+0.1% TFA

Sources & evidence

ORD record
ord-4fe7a17432f24f7bb05b040ccd4aebf8
Source dataset
uspto-grants-2012_11
Patent number
US08318667B2

Reaction notes

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