Trifluoroacetic anhydride → HCID 66643978, compound

HRID 2406639Notes

Reaction equation

HRID 2406639 reaction equation
[CH2:1]([C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH3:29][O:30][C:31](=[O:39])[CH2:32][C@H:33]([CH3:38])[CH2:34][C:35](O)=[O:36].[Cl-].[NH4+]>C1COCC1.C(Cl)Cl.C(OCC)(=O)C>[CH3:29][O:30][C:31](=[O:39])[CH2:32][CH:33]([CH3:38])[CH2:34][C:35]([N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[C:7]1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[O:36]

Participants

8

Reactant 4

HCID 9845Trifluoroacetic anhydrideHCID 25517Ammonium ChlorideHCID 6999733(R)-1-Methyl hydrogen 3-methylglutarateHCID 14299246HCID 14299246, compound

Product 1

HCID 66643978HCID 66643978, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In flask A postassium-tert-butoxide solution in THF was added to a solution of 2-hexyl-1H-indole and stirred for 30 minutes. In another flask B trifluoro acetic anhydride was added to a solution of 3(R)-methyl-pentanedioic acid monomethyl ester in methylene chloride and stirred for 20 minutes. The solution in flask A was transferred to solution in flask B and the reaction mixture was stirred for 3 hours. The reaction was treated with saturated ammonium chloride and ethyl acetate. The product was purified by column chromatography.

Workup

  1. stirringstirred for 20 minutes
  2. customThe solution in flask A was transferred to solution in flask
  3. stirringB and the reaction mixture was stirred for 3 hours
  4. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-03c3c5151ca24f3385c57d5e4f360594
Source dataset
uspto-grants-2014_08
Patent number
US08809382B2

Reaction notes

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