Trifluoroacetic acid → HCID 67056761, compound

HRID 902898Notes

Reaction equation

HRID 902898 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 to stir the mixture for 1 hour. After concentrating the reaction mixture, chloroform and a saturated aqueous solution of sodium hydrogencarbonate were added. The resultant organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by preparative thin-layer chromatography on silica gel (chloroform:methanol:water=7:3:1 under layer). A methanol solution of hydrochloric acid was added to the resultant intended product to obtain 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
  2. additiona saturated aqueous solution of sodium hydrogencarbonate were added
  3. dry with materialThe resultant organic layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resultant residue was purified by preparative thin-layer chromatography on silica gel (chloroform:methanol:water=7:3:1 under layer)
  6. additionA methanol solution of hydrochloric acid was added to the resultant

Sources & evidence

ORD record
ord-2963b6b31af0491e97bef7d3974afbc2
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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