Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 86700671, compound

HRID 1406857Notes

Reaction equation

[CH2:1]([O:8][N:9]([C@H:22]1[CH2:27][N:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:25]([C:35](=[NH:38])[NH:36][OH:37])[CH2:24][CH2:23]1)[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:39]C1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>COC(OC)OC>[CH2:1]([O:8][N:9]([C@H:22]1[CH2:27][N:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:25]([C:35]2[N:38]=[CH:39][O:37][N:36]=2)[CH2:24][CH2:23]1)[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of (2S,5R)-tert-butyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-2-(N-hydroxycarbamimidoyl)piperidine-1-carboxylate (3.0 g, 5.46 mmol), trimethoxymethane (60 mL), and PPTS (0.08 g) was stirred at 70° C. for 4 hrs. The solvent was then removed under vacuum. The residue was purified by silica gel column chromatography (gradient elution 0˜35% petroleum ether/EtOAc) to give (2S,5R)-tert-butyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-2-(1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate (2.1 g, 69%) as a yellow solid. ESI-MS (EI+, m/z): 582 [M+Na]+.

Workup

customThe solvent was then removed under vacuum
customThe residue was purified by silica gel column chromatography (gradient elution 0˜35% petroleum ether/EtOAc)

Sources & evidence

ORD record: ord-64f88a9fe3d242f09cbe07df706feba2
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916709B2

Reaction notes

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