Trifluoroacetic acid → HCID 178441323, compound

HRID 82757Notes

Reaction equation

HRID 82757 reaction equation
[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11]([C:13]2[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:14]=2[O:15][CH2:16][C@H:17]2[CH2:20][CH2:19][N:18]2C(OC(C)(C)C)=O)=[O:12])/[N:7]([CH2:36][C@H:37]2[CH2:41][CH2:40][CH2:39][O:38]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[NH:18]1[CH2:19][CH2:20][C@@H:17]1[CH2:16][O:15][C:14]1[CH:28]=[CH:29][C:30]([C:32]([F:34])([F:33])[F:35])=[CH:31][C:13]=1[C:11](/[N:10]=[C:8]1\[S:9][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:6][N:7]\1[CH2:36][C@H:37]1[CH2:41][CH2:40][CH2:39][O:38]1)=[O:12]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 178452020HCID 178452020, compound

Product 1

HCID 178441323HCID 178441323, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The mixture of Example 1B (472 mg, 0.79 mmol) and 2,2,2-trifluoroacetic acid (608 μL, 7.9 mmol) in CH2Cl2 (10 mL) was stirred at room temperature overnight. Saturated aqueous Na2CO3 (20 mL) and CH2Cl2 (20 mL) were added. The organic layer was washed with brine and concentrated. Purification by gradient flash chromatography (silica gel, 5-30% solvent A in EtOAc, solvent A: MeOH (10):Et3N (1)) afforded 330.5 mg (84%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.32 (s, 9 H), 1.56-2.00 (m, 4 H), 2.03-2.34 (m, 2 H), 3.23-3.35 (m, 2 H), 3.59-3.71 (m, 2 H), 3.74-3.83 (m, 2 H), 4.03-4.34 (m, 5 H), 7.27 (s, 1 H), 7.32 (d, J=8.81 Hz, 1 H), 7.75 (dd, J=8.98, 2.20 Hz, 1 H), 7.98 (d, J=2.37 Hz, 1 H); MS (ESI) m/z 498 (M+H)+.

Workup

  1. washThe organic layer was washed with brine
  2. concentrationconcentrated
  3. customPurification by gradient flash chromatography (silica gel, 5-30% solvent A in EtOAc, solvent A: MeOH (10):Et3N (1))

Sources & evidence

ORD record
ord-16e9bddfe3114f6ea55003d31afc57e5
Source dataset
uspto-grants-2014_09
Patent number
US08846730B2

Reaction notes

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