Trifluoroacetic acid → HCID 131732349, compound

HRID 1855158Notes

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]1[O:29][C:28]([CH2:30][CH2:31][NH:32]C(=O)OC(C)(C)C)=[N:27][N:26]=1)[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].[NH2:32][CH2:31][CH2:30][C:28]1[O:29][C:25]([C@@H:20]2[CH2:19][CH2:18][C@@H:17]3[CH2:24][N:21]2[C:22](=[O:23])[N:16]3[O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:26][N:27]=1

Participants

Conditions

Temperature: 0 °C

Procedure

TFA (0.5 mL) was added to a 0° C. solution of tert-butyl 2-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)-1,3,4-oxadiazol-2-yl)ethylcarbamate (85 mg, 0.192 mmol) in CH2Cl2 (2.0 mL). The reaction mixture was stirred at 0° C. for 2 hrs and was then concentrated under vacuum to provide (2S,5R)-2-(5-(2-aminoethyl)-1,3,4-oxadiazol-2-yl)-6-(benzyloxy)-1,6-diaza-bicyclo[3.2.1]octan-7-one TFA salt as a sticky oil, which was used directly in the next step. ESI-MS (EI+, m/z): 344.2 [M+H]+.

Workup

concentrationwas then concentrated under vacuum

Sources & evidence

ORD record: ord-7843da770b6f44c89463d6a89762bbf5
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962843B2

Reaction notes

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