Trifluoroacetic acid → Diethyl 1-[(2S)-1-aminopropan-2-yl]-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

HRID 1521724Notes

Reaction equation

HRID 1521724 reaction equation
C(OC([NH:8][CH2:9][C@@H:10]([N:12]1[C:16]2=[N:17][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:20]=[C:15]2[CH:14]=[C:13]1[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH3:11])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH2:9][C@@H:10]([N:12]1[C:16]2=[N:17][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:20]=[C:15]2[CH:14]=[C:13]1[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH3:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67238103Diethyl (S)-1-(1-((tert-butoxycarbonyl)amino)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

Product 1

HCID 67236980Diethyl 1-[(2S)-1-aminopropan-2-yl]-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl 1-{(2S)-1-[(tert-butoxycarbonyl)amino]propan-2-yl}-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (3.00 g, 7.15 mmol) in CH2Cl2 (20 mL) is added TFA (10 mL). The mixture is stirred at room temperature for 3 hr then is concentrated under reduced pressure. The residue is taken up in ethyl acetate and is washed with brine, is dried (Na2SO4) and concentrated in vacuo to afford the title compound (2.17 g) which is used in the next step without purification.

Workup

  1. concentrationthen is concentrated under reduced pressure
  2. washis washed with brine
  3. dry with materialis dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-59eb7f3fe701497ba6ae9ac180eae63e
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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