Trifluoroacetic acid → HCID 131732350, compound

HRID 870830Notes

Reaction equation

HRID 870830 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[CH2:8]([O:15][N:16]1[C:22](=[O:23])[N:21]2[CH2:24][C@H:17]1[CH2:18][CH2:19][C@H:20]2[C:25]([NH:27][NH:28]C(OC(C)(C)C)=O)=[O:26])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[OH:7][C:1]([C:3]([F:6])([F:5])[F:4])=[O:2].[CH2:8]([O:15][N:16]1[C:22](=[O:23])[N:21]2[CH2:24][C@H:17]1[CH2:18][CH2:19][C@H:20]2[C:25]([NH:27][NH2:28])=[O:26])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86701380HCID 86701380, compound

Product 1

HCID 131732350HCID 131732350, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (15 mL) was added dropwise to a solution of tert-butyl 2-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbonyl)hydrazinecarboxylate (3 g, 7.7 mmol) in DCM (30 mL) at 0° C. The resulting mixture was stirred at rt for 1 h, and then concentrated. The residue was further dried under high vacuum and washed with Et2O (3×) to afford (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide TFA salt (3 g, 93%) as a white solid. ESI-MS (EI+, m/z): 291 [M+H]+.

Workup

  1. concentrationconcentrated
  2. customThe residue was further dried under high vacuum
  3. washwashed with Et2O (3×)

Sources & evidence

ORD record
ord-08e1d3c0320c41fca37049b42d627432
Source dataset
uspto-grants-2015_03
Patent number
US08969570B2

Reaction notes

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