Acetic Acid → HCID 69048143, compound

HRID 1867738Notes

Reaction equation

[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(O)(=O)C.O=[C:15]1[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]1.[C-:26]#[N:27].[Na+]>O.C(OCC)C>[CH2:3]([N:2]([CH3:1])[C:15]1([C:26]#[N:27])[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Methylbenzylamine (1.42 ml, 11 mmol) and acetic acid (0.63 ml, 11 mmol) in 2 ml of water were added to a solution of tert-butyl 3-oxoazetidine-1-carboxylate (1.5 g, 8.77 mmol) in diethylether (1.5 ml). After five minutes, a solution of sodium cyanide (451 mg, 9.21 mmol) in 1 ml of water was added, and the mixture was heated at 60° C. for 15 hours. After cooling the reaction mixture was extracted with ethyl acetate (×2), washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residues were purified by column chromatography on silica eluting with ethyl acetate in petroleum ether (5/95) to give tert-butyl 3-[benzyl(methyl)amino]-3-cyanoazetidine-1-carboxylate as a pale yellow oil, (2.52 g, 96%); 1H NMR Spectrum: (CDCl3) 1.46 (s, 9H), 2.18 (s, 3H), 3.42 (s, 2H), 4.00 (d, 2H), 4.17 (d, 2H), 7.26-7.35 (m, 5H).

Workup

temperatureAfter cooling the reaction mixture
extractionwas extracted with ethyl acetate (×2)
washwashed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting residues were purified by column chromatography on silica eluting with ethyl acetate in petroleum ether (5/95)

Sources & evidence

ORD record: ord-93d2dd92ee38498c8f238bce84c28bd9
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632840B2

Reaction notes

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