Trifluoroacetic acid → HCID 76571769, compound

HRID 70484Notes

Reaction equation

HRID 70484 reaction equation
C(OC(=O)[NH:7][CH:8]([C:10](=[O:73])[NH:11][CH:12]([C:16]([N:18]1[CH2:22][CH2:21][CH2:20][CH:19]1[CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:26]([CH2:33][C:34]#[C:35][C:36]#[C:37][CH2:38][N:39]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:41]([CH2:48][CH:49]3[CH2:53][CH2:52][CH2:51][N:50]3[C:54](=[O:72])[CH:55]([NH:59][C:60](=[O:71])[CH:61]([NH:63]C(OC(C)(C)C)=O)[CH3:62])[CH:56]([CH3:58])[CH3:57])=[CH:40]2)[CH:25]=1)=[O:17])[CH:13]([CH3:15])[CH3:14])[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:63][CH:61]([CH3:62])[C:60]([NH:59][CH:55]([C:54]([N:50]1[CH2:51][CH2:52][CH2:53][CH:49]1[CH2:48][C:41]1[C:42]2[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=2)[N:39]([CH2:38][C:37]#[C:36][C:35]#[C:34][CH2:33][N:26]2[C:27]3[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:24]([CH2:23][CH:19]3[CH2:20][CH2:21][CH2:22][N:18]3[C:16](=[O:17])[CH:12]([NH:11][C:10](=[O:73])[CH:8]([NH2:7])[CH3:9])[CH:13]([CH3:15])[CH3:14])=[CH:25]2)[CH:40]=1)=[O:72])[CH:56]([CH3:57])[CH3:58])=[O:71]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 76187927HCID 76187927, compound

Product 1

HCID 76571769HCID 76571769, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 42 (0.030 g, 0.029 mmol) in DCM (5 mL) was added TFA (1 mL) and the reaction mixture was stirred at room temperature for 30 min. Aqueous NaHCO3 (3 mL) was then added to the reaction mixture. The reaction mixture was concentrated, diluted with water, and the product was extracted with DCM (3×30 mL). The organic extracts were washed with water, brine and dried over anhydrous Na2SO4. The solvent was removed on rotary evaporator and the product was purified by reverse phase HPLC. 1H NMR (DMSO, 300 MHz) δ8.0 (s, 2H), 7.9 (d, J=9.9 Hz, 2H), 7.38 (d, J=9.9 Hz, 2H), 7.3-7.1 (m, 6H), 6.8 (m, 2H), 4.8 (s, 4H), 4.62 (m 2H), 4.5-4.4 (m 2H), 4.4-4.0 (m, 4H), 3.7-3.5 (m, 4H), 3.4 (m, 2H), 2.5 (m, 2H), 2.2-1.8 (m, 8H), 1.35 (d, J=9.9 Hz, 6H), 1.05 (d, J=5.5 Hz, 6H), 0.95 (d, J=5.5 Hz, 6H) ppm.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. extractionthe product was extracted with DCM (3×30 mL)
  4. washThe organic extracts were washed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was removed on rotary evaporator
  7. customthe product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-828cb2b2557c458999e5c03bbdad1b27
Source dataset
uspto-grants-2014_09
Patent number
US08822525B2

Reaction notes

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