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Trifluoroacetic acid → tert-butyl (3R)-3-(aminooxy)pyrrolidine-1-carboxylate

HRID 330897
Notes
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Reaction equation

HRID 330897 reaction equation
O=C1N2C[C@@H](CC[C@H]2C([NH:12][O:13][C@H:14]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15]2)=O)N1OS(O)(=O)=O.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:12][O:13][C@@H:14]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86693917tert-Butyl (3S)-3-[({[(2S,5R)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]pyrrolidine-1-carboxylate

Product 1

HCID 86693911tert-butyl (3R)-3-(aminooxy)pyrrolidine-1-carboxylateYield 62.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of tert-butyl (3S)-3-[({[(2S,5R)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]pyrrolidine-1-carboxylate 10 (0.11 g, 0.24 mmol) in DCM (4.0 mL) was added trifluoroacetic acid (0.20 mL) at 0° C. The mixture was stirred at 0° C. for 1 h, concentrated and washed with ether. The white solid was collected by centrifugation. The crude product was purified by preparative HPLC to provide Compound 2 (Table 1) (30.4 mg, 36%) as a white solid.

Workup

  1. concentrationconcentrated
  2. washwashed with ether
  3. customThe white solid was collected by centrifugation
  4. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-cca5b0c48d4b4526b5551d66e96eb206
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08877743B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes