Trifluoroacetic acid → HCID 86700689, compound

HRID 870836Notes

Reaction equation

HRID 870836 reaction equation
C(O)(C(F)(F)F)=O.[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]1[O:29][C:28]([CH:30]2[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]2)=[N:27][N:26]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[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]1[O:29][C:28]([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[N:27][N:26]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86701384HCID 86701384, compound

Product 1

HCID 86700689HCID 86700689, compoundYield 171.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

CF3COOH (5 mL) was slowly added to a solution of tert-butyl 4-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)-1,3,4-oxadiazol-2-yl)piperidine-1-carboxylate (719 mg, 1.5 mmol) in DCM (20 mL) at 0° C. The mixture was stirred at 0° C. for 3 hrs then, the solvent was concentrated in vacuum to afford (2S,5R)-6-(benzyloxy)-2-(5-(piperidin-4-yl)-1,3,4-oxadiazol-2-yl)-1,6-diaza-bicyclo[3.2.1]octan-7-one (988 mg) as a brown oil, which was used directly in the next step. ESI-MS (EI+, m/z): 384.1 [M+H]+.

Workup

  1. concentrationthe solvent was concentrated in vacuum

Sources & evidence

ORD record
ord-4f20974c719f470da15a3035ef53a4d8
Source dataset
uspto-grants-2015_03
Patent number
US08969570B2

Reaction notes

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