4-Bromophenacyl bromide → HCID 56962039, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][CH3:14])[CH2:10][C@H:9]1[C:15](O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:18][C:19]1[CH:28]=[CH:27]C(C(=O)CBr)=[CH:21][CH:20]=1.C([N:32](CC)[CH:33]([CH3:35])[CH3:34])(C)C.C([O-])(=O)C.[NH4+:42]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][CH3:14])[CH2:10][C@H:9]1[C:15]1[NH:32][C:33]([C:34]2[CH:27]=[CH:28][C:19]([Br:18])=[CH:20][CH:21]=2)=[CH:35][N:42]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]Participants
Conditions
- Temperature
- 35 °C
Procedure
To a solution of (2S,4S)-4-methoxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (900 mg, 3.67 mmol), and p-bromophenacyl bromide (1.02 g, 3.67 mmol) in DCM (20 mL) under nitrogen, was added N,N-diisopropylethylamine (1.92 mL, 11.01 mmol). The resulting mixture was stirred at 35° C. for 3 h and concentrated under vacuum. The crude intermediate was dissolved in toluene (150 mL), ammonium acetate (5.66 g, 73.4 mmol) was added, and the resulting mixture was stirred at 95° C. overnight, cooled to RT, and washed with water (2×10 mL). The organic layer was dried over magnesium sulfate, filtered, concentrated and purified by silica gel chromatography (24 g, ethyl acetate/hexanes 0 to 60%) to give the title intermediate (1.49 g, 96% yield).
Workup
- concentrationconcentrated under vacuum
- dissolutionThe crude intermediate was dissolved in toluene (150 mL)
- stirringthe resulting mixture was stirred at 95° C. overnight
- temperaturecooled to RT
- washwashed with water (2×10 mL)
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- custompurified by silica gel chromatography (24 g, ethyl acetate/hexanes 0 to 60%)
Sources & evidence
- ORD record
- ord-39f2ffc450a34c12b083a48bf925c29c
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206159B2
Reaction notes
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