Trifluoroacetic acid → HCID 86654209, compound

HRID 1968274Notes

Reaction equation

HRID 1968274 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-55832bbc04f14476801b0b97c08aa18e
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

Loading…