Trifluoroacetic acid → HCID 178441322, compound

HRID 82758Notes

Reaction equation

HRID 82758 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 178452021HCID 178452021, compound

Product 1

HCID 178441322HCID 178441322, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The mixture of Example 2A (478 mg, 0.8 mmol) and 2,2,2-trifluoroacetic acid (616 μL, 8.0 mmol) in CH2Cl2 (10 mL) was stirred at ambient temperature overnight. Saturated aqueous Na2CO3 (20 mL) was added followed by CH2Cl2 (30 mL). The organic layer was washed with brine and concentrated. Purification by gradient flash chromatography (silica gel, 5-30% (Et3N:MeOH, 1:10)/EtOAc) afforded 340 mg (85%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.32 (s, 9 H), 1.55-1.98 (m, 4 H), 2.04-2.34 (m, 2 H), 3.25-3.51 (m, 1 H), 3.59-3.87 (m, 4 H), 4.01-4.39 (m, 6 H), 7.26 (s, 1 H), 7.32 (d, J=8.73 Hz, 1 H), 7.74 (dd, J=8.73, 2.78 Hz, 1 H), 7.98 (d, J=2.38 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% (Et3N:MeOH, 1:10)/EtOAc)

Sources & evidence

ORD record
ord-cc9b3320a488454f93ea8903996aeef0
Source dataset
uspto-grants-2014_09
Patent number
US08846730B2

Reaction notes

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