Potassium Carbonate → Methyl 2-((tert-butoxycarbonyl)amino)prop-2-enoate

HRID 339015Notes

Reaction equation

C(OC(O[CH2:12][C@H:13]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:22]([O:21][C:19]([NH:18][C:13](=[CH2:12])[C:14]([O:16][CH3:17])=[O:15])=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of (S)-methyl 3-(benzyloxycarbonyloxy)-2-(tert-butoxycarbonylamino)propanoate (36.0 g, 102 mmol), K2CO3 (28.2 g, 204 mmol) and DMF (204 mL) was heated at 65° C. for 1 hour. After cooling, the reaction mixture was partitioned between ether and water. The aqueous layer was extracted with ether. The combined organic layers were washed with water and brine, dried and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (10:1 hexanes/EtOAc) to give methyl 2-(tert-butoxycarbonylamino)acrylate (16.5 g, 81%) as a colorless oil, which was used directly in the next step.

Workup

temperatureAfter cooling
customthe reaction mixture was partitioned between ether and water
extractionThe aqueous layer was extracted with ether
washThe combined organic layers were washed with water and brine
customdried
concentrationconcentrated under reduced pressure
customThe residue was purified by flash chromatography on silica gel (10:1 hexanes/EtOAc)

Sources & evidence

ORD record: ord-10c7dff811de4509b262b6f7d92fa579
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889704B2

Reaction notes

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