Ethyl Acetate → HCID 67970625, compound
Reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[C:6]([O:10][C:11](=[O:20])[NH:12][CH2:13][C:14](=[O:19])N(OC)C)([CH3:9])([CH3:8])[CH3:7].C(OCC)(=O)C>O1CCCC1>[C:6]([O:10][C:11](=[O:20])[NH:12][CH2:13][C:14]([CH:1]1[CH2:3][CH2:2]1)=[O:19])([CH3:7])([CH3:8])[CH3:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
To 22 ml of a 0.5M solution of cyclopropylmagnesium bromide in tetrahydrofuran was added 2.2 g [(methoxy-methyl-carbamoyl)-methyl]-carbamic acid tert-butyl ester at −10° C. (acetone/ice) and the mixture was stirred at −10° C. for 30 min and then at ambient temperature for 30 min. (tic shows little conversion heptanes:ethyl acetate=1:1) To the resulting colorless solution was added another 22 ml of a 0.5M solution of cyclopropylmagnesium bromide in tetrahydrofuran and the mixture was stirred at ambient temperature for 18 h. The reaction mixture was quenched by addition of 10% citric acid. The phases were separated and the organic phase was purified by chromatography on silica gel with a gradient of heptane:ethyl acetate=9:1 to 1:1 to yield 1.300 g of the title compound as colorless oil. MS (EI): 199 (M+).
Workup
- stirringthe mixture was stirred at ambient temperature for 18 h
- customThe reaction mixture was quenched by addition of 10% citric acid
- customThe phases were separated
- customthe organic phase was purified by chromatography on silica gel with a gradient of heptane
Sources & evidence
- ORD record
- ord-6364b08a82064d70b423d6391a958459
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08669254B2
Reaction notes
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