Trifluoroacetic acid → HCID 67056761, compound

HRID 2104452Notes

Reaction equation

HRID 2104452 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][C@H:14]1[C@H:18]([NH:19][C:20]([C:22]3[S:23][C:24]4[CH2:25][N:26]([CH3:31])[CH2:27][CH2:28][C:29]=4[N:30]=3)=[O:21])[CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]1)=[O:12])=[CH:5]2.FC(F)(F)C(O)=O>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][C@@H:14]1[CH2:15][NH:16][CH2:17][C@H:18]1[NH:19][C:20]([C:22]1[S:23][C:24]3[CH2:25][N:26]([CH3:31])[CH2:27][CH2:28][C:29]=3[N:30]=1)=[O:21])=[O:12])=[CH:5]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59676994HCID 59676994, compound

Product 1

HCID 67056761HCID 67056761, compoundYield 119.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (170 mg) obtained in Example 94 was dissolved in methylene chloride (3 mL), and trifluoroacetic acid (2 mL) was added at room temperature, followed by stirring for 1 hour. After concentrating the reaction mixture, chloroform and saturated aqueous sodium hydrogencarbonate were added. The resultant organic layer was dried over sodium sulfate anhydrate, and the solvent was distilled away under reduced pressure. The resultant residue was purified by silica gel thin layer chromatography (chloroform:methanol:water=7:3:1, under layer). HCl in methanol was added to the resultant product to give the title compound (90 mg) as a hydrochloride (NMR was measured in the form of a free base).

Workup

  1. concentrationAfter concentrating the reaction mixture, chloroform and saturated aqueous sodium hydrogencarbonate
  2. additionwere added
  3. dry with materialThe resultant organic layer was dried over sodium sulfate anhydrate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resultant residue was purified by silica gel thin layer chromatography (chloroform:methanol:water=7:3:1, under layer)
  6. additionHCl in methanol was added to the resultant product

Sources & evidence

ORD record
ord-57ee81002af6499384a131288437da11
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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