Methanol → (9H-fluoren-9-yl)methyl 4-(5-((2S,5R)-6-hydroxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate

HRID 1406875Notes

Reaction equation

B(Cl)(Cl)Cl.C([O:12][N:13]1[C:19](=[O:20])[N:18]2[CH2:21][C@H:14]1[CH2:15][CH2:16][C@H:17]2[C:22]1[O:26][N:25]=[C:24]([CH:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][CH2:36][CH:37]3[C:49]4[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=4[C:43]4[C:38]3=[CH:39][CH:40]=[CH:41][CH:42]=4)=[O:34])[CH2:29][CH2:28]2)[N:23]=1)C1C=CC=CC=1.CO>C(Cl)Cl>[OH:12][N:13]1[C:19](=[O:20])[N:18]2[CH2:21][C@H:14]1[CH2:15][CH2:16][C@H:17]2[C:22]1[O:26][N:25]=[C:24]([CH:27]2[CH2:28][CH2:29][N:30]([C:33]([O:35][CH2:36][CH:37]3[C:49]4[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=4[C:43]4[C:38]3=[CH:39][CH:40]=[CH:41][CH:42]=4)=[O:34])[CH2:31][CH2:32]2)[N:23]=1

Participants

Conditions

Temperature: -78 °C

Procedure

BCl3 (8.5 ml, 8.5 mmol; 1 M in CH2Cl2) was added dropwise to a solution of (9H-fluoren-9-yl)methyl 4-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate (1.0 g, 1.7 mmol, 1.0 eq.) in dried CH2Cl2 (20 mL) at −78° C. The mixture was stiffed under N2 atmosphere at 0° C. for 6 hrs. Then, the reaction mixture was cooled to −78° C. and MeOH (2 mL) was added dropwise. The solvents were evaporated under vacuum at 0° C. to give ((9H-fluoren-9-yl)methyl 4-(5-((2S,5R)-6-hydroxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate (970 mg) as a yellow solid, which was used directly in the next step. ESI-MS (EI−, m/z): 516.3 [M+H]−.

Workup

customThe solvents were evaporated under vacuum at 0° C.

Sources & evidence

ORD record: ord-5a446890457345b69230e9f1ba0a54b8
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916709B2

Reaction notes

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