Trifluoroacetic acid → HCID 54673532, compound

HRID 509538Notes

Reaction equation

HRID 509538 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[C:14]([C:15]2[O:19][C:18]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][N:27](C)[C:28](=O)OC(C)(C)C)=[CH:22][CH:21]=3)=[N:17][N:16]=2)=[CH:13][C:12]([C:36]2[CH:41]=[CH:40][C:39]([S:42]([CH:45]([CH3:47])[CH3:46])(=[O:44])=[O:43])=[CH:38][N:37]=2)=[CH:11][N:10]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:45]([S:42]([C:39]1[CH:40]=[CH:41][C:36]([C:12]2[CH:13]=[C:14]([C:15]3[O:19][C:18]([C:20]4[CH:21]=[CH:22][C:23]([CH2:26][NH:27][CH3:28])=[CH:24][CH:25]=4)=[N:17][N:16]=3)[C:9]([NH2:8])=[N:10][CH:11]=2)=[N:37][CH:38]=1)(=[O:43])=[O:44])([CH3:47])[CH3:46]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68104456HCID 68104456, compound

Product 1

HCID 54673532HCID 54673532, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The residue from Method F Step 2 was dissolved in DCM (10 mL) and TFA (2 mL, 25.96 mmol) was added. The reaction was stirred at ambient temperature for 15 hours. The solvent was removed in vacuo and the residue azeotroped with DCM (×2) and ether (×2). The material was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, passed through a sodium bicarbonate cartridge and freeze-dried to give the title compound as an off-white solid (11.4 mg, 16% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.23 (d, J=6.8 Hz, 6H), 2.30 (s, 3H), 3.56 (sept, 1H), 3.77 (s, 2H), 7.60 (d, 2H), 7.91 (s, 2H), 8.16 (d, 2H), 8.29 (dd, 1H), 8.36 (d, 1H), 9.00 (d, 1H), 9.03 (d, 1H) and 9.12 (d, 1H) ppm; MS (ES+) 465.3.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue azeotroped with DCM (×2) and ether (×2)
  3. customThe material was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]
  4. customThe fractions were collected
  5. customfreeze-dried

Sources & evidence

ORD record
ord-62d0c98abd544cc8ae0b74c792724ef7
Source dataset
uspto-grants-2015_08
Patent number
US09096584B2

Reaction notes

Loading…