Methanol → HCID 11164640, compound

HRID 1026672Notes

Reaction equation

[C-:1]#[N:2].[K+].[O:4]1[C:6]2([CH2:11][CH2:10][N:9]([C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:22][C@H:21]([CH2:23][NH:24][C:25](=[O:27])[CH3:26])[O:20][C:19]4=[O:28])=[CH:14][CH:13]=3)[CH2:8][CH2:7]2)[CH2:5]1.CO>CN(C)C=O>[C:1]([CH2:5][C:6]1([OH:4])[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:22][C@H:21]([CH2:23][NH:24][C:25](=[O:27])[CH3:26])[O:20][C:19]3=[O:28])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)#[N:2]

Participants

Conditions

Temperature: 25 °C

Procedure

The title compound was prepared by reacting potassium cyanide (20.7 mmol) with (S)—N-{3-[4-(1-oxa-6-aza-spiro[2.5]oct-6-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (13.8 mmol) in 60 ml 5:1 methanol: dimethylformamide mixture under stirring. The reaction was stirred for 12 hours at 25° C. and quenched with saturated ferrous sulfate solution. The reaction mixture was filtered. The filtrate was extracted with ethyl acetate, organic layer was washed with brine and dried over sodium sulfate. Evaporation of organic solvent under vacuum and silica gel chromatographic purification afforded the titled product in 44% yield. M.P. 88-90° C. and MS (M+1)=373 (MH+, 100%) for M.F.=C19H24N4O4.

Workup

customThe title compound was prepared
customquenched with saturated ferrous sulfate solution
filtrationThe reaction mixture was filtered
extractionThe filtrate was extracted with ethyl acetate, organic layer
washwas washed with brine
dry with materialdried over sodium sulfate
customEvaporation of organic solvent
customunder vacuum and silica gel chromatographic purification

Sources & evidence

ORD record: ord-ea50a32b2f974048a2fdc2786831ddcf
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729269B2

Reaction notes

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