cis Ethyl 3-bromo-2-oxo-1-azacyclodecane-10-carboxylate → cis Ethyl 3-acetoxy-2-oxo-1-azacyclodecane-10-carboxylate

HRID 21964

Reaction equation

Br[C@H:2]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C@@H:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:4][C:3]1=[O:17]>CN(C)C=O.C(OCC)(=O)C.C([O-])(=O)C.[Ag+]>[C:12]([O:14][C@H:2]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C@@H:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:4][C:3]1=[O:17])(=[O:13])[CH3:5]

Participants

Conditions

Temperature: 100 °C

Procedure

Cis ethyl 3-bromo-2-oxo-1-azacyclodecane-10-carboxylate (2.96 g, 9.67 mmol) is dissolved in dimethylformamide (30 mL). Silver acetate (6.35 g, 38 mmol) is added, and the reaction is heated to 100° C. for 3 hours. After cooling back to room temperature, the reaction is diluted with ethyl acetate (100 mL), filtered through a pad of silica gel, and the solvent is evaporated to give crude cis ethyl 3-acetoxy-2-oxo-1-azacyclodecane-10-carboxylate.

Workup

temperatureAfter cooling back to room temperature
filtrationfiltered through a pad of silica gel
customthe solvent is evaporated

Sources & evidence

ORD record: ord-4ab851271b6e4206b930e0cfb2571b4e
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05426103

Linked notes

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