Ethyl Acetate → HCID 58762326, compound
Reaction equation
[Li+].CC([N-]C(C)C)C.[CH3:9][CH2:10][O:11][C:12]([CH3:14])=[O:13].[CH:15]1([C:20](=[O:33])[CH2:21][CH2:22][NH:23][C:24](=[O:32])[CH2:25][CH2:26][C:27]2[O:28][CH:29]=[CH:30][CH:31]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1>C1COCC1>[CH:15]1([C:20]([OH:33])([CH2:21][CH2:22][NH:23][C:24](=[O:32])[CH2:25][CH2:26][C:27]2[O:28][CH:29]=[CH:30][CH:31]=2)[CH2:14][C:12]([O:11][CH2:10][CH3:9])=[O:13])[CH2:16][CH2:17][CH2:18][CH2:19]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -40 °C
Procedure
To a solution of LDA (1.0 M, 1.1 mL, 1.1 mmol) cooled to −78° C. was added EtOAc (0.1 mL, 1.1 mmol). After stirring for 30 minutes, a solution of N-(3-cyclopentyl-3-oxo-propyl)-3-furan-2-yl-propionamide (100 mg, 0.38 mmol; described in Step 2 of example H(4)) dissolved in 3 mL THF was added. The reaction was stirred for 2 hours and then allowed to warm to −40° C. The reaction was quenched with 10 mL saturated NH4Cl, and the layers were separated. The aqueous layer was extracted with 3×10 mL CH2Cl2, and the organic layers were combined. After concentrating the organic layers by rotary evaporation, the product was purified by flash chromatography (86 mg, 64% yield). MS (ESI): 350 (M−H).
Workup
- additionwas added
- stirringThe reaction was stirred for 2 hours
- customThe reaction was quenched with 10 mL saturated NH4Cl
- customthe layers were separated
- extractionThe aqueous layer was extracted with 3×10 mL CH2Cl2
- concentrationAfter concentrating the organic layers
- customby rotary evaporation
- customthe product was purified by flash chromatography (86 mg, 64% yield)
Sources & evidence
- ORD record
- ord-f0556be263c04f218456b6ae0ae71cdf
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473790B2
Reaction notes
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