Pyridine → HCID 11458610, compound
Reaction equation
[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@@H:9]1[C:10](O)=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].N1C(F)=NC(F)=NC=1[F:18].N1C=CC=CC=1>C(Cl)Cl>[C:4]([O:3][C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@@H:9]1[C:10]([F:18])=[O:11])=[O:2])([CH3:7])([CH3:6])[CH3:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -15 °C
Procedure
To an oven-dried, septaed 10 mL round-bottom flask, cooled under an argon atmosphere, and charged with (R)-N-BOC-proline, 24d, (215.3 mg, 1.00 mmol) was added 2.5 mL freshly distilled CH2Cl2 under argon. The reaction was cooled to −15° C. and to the flask was added cyanuric fluoride (450 μL, 5 mmol). The reaction was stirred at −15° C. for 15 minutes then anhydrous pyridine (81 μL, 1.0 mmol) was added. Stirring was maintained at −15° C. for 90 minutes. Without warming, the crude reaction was poured over ice, and immediately extracted twice with CH2Cl2. The combined CH2Cl2 extracts were washed once with water, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford 170.3 mg of 25d as a colorless oil. FTIR (neat) 1850 cm−1.
Workup
- temperaturecooled under an argon atmosphere
- stirringStirring
- temperaturewas maintained at −15° C. for 90 minutes
- temperatureWithout warming
- customthe crude reaction
- additionwas poured over ice
- extractionimmediately extracted twice with CH2Cl2
- washThe combined CH2Cl2 extracts were washed once with water
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-2c259698fe78455ea172f6100d2c77c3
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07045360B2
Reaction notes
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