Stannane, hydroxytrimethyl- → 2-(o-Toluidino)-5-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl)oxazole-4-carboxylic acid

HRID 1410491Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of tert-butyl 4-(4-(2-(o-toluidino)-4-(ethoxycarbonyl)oxazol-5-yl)phenyl)piperazine-1-carboxylate (0.042 g, 0.08 mmol) in DCE (2 ml) was added trimethyltin hydroxide (0.140 g, 0.77 mmol) and the resulting mixture was heated at 80° C. overnight. The reaction was cooled to room temperature and diluted with DCM. The organic phase was washed with water. The combined aqueous phase was extracted with DCM and the combined organic phase dried over MgSO4 and the solvent removed in vacuo to afford 2-(o-toluidino)-5-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl)oxazole-4-carboxylic acid (0.038 g, 0.08 mmol, 96%). LCMS (1) Rt: 1.89 min; m/z (ES+) 479.

Workup

temperatureThe reaction was cooled to room temperature
washThe organic phase was washed with water
extractionThe combined aqueous phase was extracted with DCM
dry with materialthe combined organic phase dried over MgSO4
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-96e36f484db947c7b3c8903042e531ae
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921544B2

Reaction notes

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