Trifluoroacetic acid → (S)-ethyl 1-((S)-2-amino-2-(tetrahydro-2H-pyran-4-yl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

HRID 627056Notes

Reaction equation

HRID 627056 reaction equation
C(OC([NH:8][C@@H:9]([CH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)[C:10]([N:12]1[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[CH2:14][C@H:13]1[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:11])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C@@H:9]([CH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)[C:10]([N:12]1[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[CH2:14][C@H:13]1[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735271(S)-ethyl 1-((S)-2-(tert-butoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Product 1

HCID 131735272(S)-ethyl 1-((S)-2-amino-2-(tetrahydro-2H-pyran-4-yl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylateYield 82.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 100 mL round-bottomed flask, (S)-ethyl 1-((S)-2-(tert-butoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (220 mg, 507 μmol, Eq: 1.00) was combined with DCM (10 mL) to give a colorless solution. TFA (5 mL, 64.9 mmol, Eq: 128) was added and the reaction was stirred at rt for 2 h. The reaction mixture was concentrated in vacuo and the residue was treated with saturated aqueous NaHCO3 (10 mL). The resulting mixture was extracted with DCM (2×10 mL), the combined organic layers dried over Na2SO4, and then concentrated in vacuo to give (S)-ethyl 1-((S)-2-amino-2-(tetrahydro-2H-pyran-4-yl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (140 mg), m/z=334 (M+H).

Workup

  1. customto give a colorless solution
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionthe residue was treated with saturated aqueous NaHCO3 (10 mL)
  4. extractionThe resulting mixture was extracted with DCM (2×10 mL)
  5. dry with materialthe combined organic layers dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cacf6f0bd5e346d7803e4c7d9cfedeaf
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

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