Trifluoroacetic acid → HCID 86654209, compound

HRID 1627178Notes

Reaction equation

HRID 1627178 reaction equation
C([O:5][C:6](=[O:32])[C@H:7]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]2[N:18](C(OC(C)(C)C)=O)[CH:19]=[C:20]([C:21]([O:23][CH3:24])=[O:22])[C:13]=12)[CH2:8][CH3:9])(C)(C)C.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>C(Cl)Cl>[F:36][C:35]([F:38])([F:37])[C:33]([OH:39])=[O:34].[CH3:24][O:23][C:21]([C:20]1[C:13]2[C:14](=[N:15][CH:16]=[CH:17][C:12]=2[CH2:11][NH:10][C@H:7]([CH2:8][CH3:9])[C:6]([OH:32])=[O:5])[NH:18][CH:19]=1)=[O:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58293538HCID 58293538, compound

Product 1

HCID 86654209HCID 86654209, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 100 mL round bottom flask equipped for stirring was added (R)-1-tert-butyl 3-methyl 4-((1-tert-butoxy-1-oxobutan-2-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate (1.45 g, 3.24 mmol) and DCM (10 mL). TFA (10 mL) was added and the reaction mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated and dried in vacuo to afford the title compound as a yellow oil (1.3 g, 99%) (TFA salt). [M+H] calc'd for C14H17N3O4, 292; found, 292.6.

Workup

  1. customTo a 100 mL round bottom flask equipped
  2. stirringthe reaction mixture was stirred at room temperature for 30 min
  3. concentrationThe reaction mixture was concentrated
  4. customdried in vacuo

Sources & evidence

ORD record
ord-31c64042cb56496e9c5a83484e7ba23e
Source dataset
uspto-grants-2014_07
Patent number
US08785429B2

Reaction notes

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