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

HRID 389762Notes

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-c43d00294ba243fea14043d48570f5d5
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378095B2

Reaction notes

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