Hydrochloric Acid → (S)-ethyl 1-((S)-2-amino-3-methylbutanoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate hydrochloride

HRID 525292Notes

Reaction equation

HRID 525292 reaction equation
C(OC([NH:8][C@@H:9]([CH:26]([CH3:28])[CH3:27])[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.[ClH:29]>CCO>[ClH:29].[NH2:8][C@@H:9]([CH:26]([CH3:27])[CH3:28])[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 313Hydrochloric AcidHCID 131735584(S)-ethyl 1-((S)-2-(tert-butoxycarbonylamino)-3-methylbutanoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Product 1

HCID 131735254(S)-ethyl 1-((S)-2-amino-3-methylbutanoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate hydrochlorideYield 100.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S)-ethyl 1-((S)-2-(tert-butoxycarbonylamino)-3-methylbutanoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (1.9 g, 4.85 mmol, Eq: 1.00) in EtOH (10.1 mL) was added HCl (2 M in ether, 38.0 mL, 76.0 mmol, Eq: 15.7) and the resulting solution was stirred at rt overnight. The reaction mixture was concentrated in vacuo and azeotroped with n-heptane (1×75 mL) to give (S)-ethyl 1-((S)-2-amino-3-methylbutanoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate hydrochloride as a white solid (1.6 g).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customazeotroped with n-heptane (1×75 mL)

Sources & evidence

ORD record
ord-251599bca31a4d7dbb5b30fa34a979dd
Source dataset
uspto-grants-2016_05
Patent number
US09340573B2

Reaction notes

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