Trifluoroacetic acid → (R)-methyl 1-((S)-3-amino-2-(benzyloxycarbonylamino)propanoyl)piperidine-2-carboxylate trifluoroacetate

HRID 529492Notes

Reaction equation

HRID 529492 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:25][NH:26]C(OC(C)(C)C)=O)[C:13]([N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@@H:16]1[C:21]([O:23][CH3:24])=[O:22])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:34]([OH:40])([C:36]([F:39])([F:38])[F:37])=[O:35]>C(Cl)Cl>[F:37][C:36]([F:39])([F:38])[C:34]([OH:40])=[O:35].[NH2:26][CH2:25][C@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[C:13]([N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@@H:16]1[C:21]([O:23][CH3:24])=[O:22])=[O:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68292412(R)-methyl 1-((S)-2-(benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)propanoyl)piperidine-2-carboxylate

Product 1

HCID 86706206(R)-methyl 1-((S)-3-amino-2-(benzyloxycarbonylamino)propanoyl)piperidine-2-carboxylate trifluoroacetateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask was added (R)-methyl 1-((S)-2-(benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)propanoyl)piperidine-2-carboxylate (1.80 gm, 3.88 mmol), DCM (5 mL) and TFA (5 mL). The reaction mixture was stirred at rt for 1 hr. The reaction mixture was then concentrated and dried under vacuum for 3 hr to afford (R)-methyl 1-((S)-3-amino-2-(benzyloxycarbonylamino)propanoyl)piperidine-2-carboxylate trifluoroacetate (1.87 g, 3.92 mmol, 100% yield) as a colorless oil. Anal. Calcd. for C18H25N3O5 m/z 363.4. found: 364.3 (M+H)+.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customdried under vacuum for 3 hr

Sources & evidence

ORD record
ord-e94db5dab8eb42039c595017b4ee7d87
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

Loading…