Pivaloyl chloride → HCID 66934181, compound
Reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([Cl:19])=[C:16](Cl)[S:17][C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[CH3:25][C:26]([CH3:31])([CH3:30])[C:27](Cl)=[O:28]>C1COCC1.CCCCCC>[CH2:1]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([Cl:19])=[C:16]([C:27](=[O:28])[C:26]([CH3:31])([CH3:30])[CH3:25])[S:17][C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
The product from step (g) (109 mg, 0.35 mmol) in anhydrous THF (5 ml) was cooled to −78° C. under a nitrogen atmosphere and treated with 1.6 M n-butyl lithium in hexane (0.25 ml). The reaction mixture was stirred at −78° C. for 5 minutes followed by the addition of trimethyl acetyl chloride (0.22 ml, 1.75 mmol). After 10 additional minutes at −78° C., the reaction mixture was allowed to warm to room temperature. The reaction was quenched with saturated NaHCO3 (20 ml) and extracted with ethyl acetate (3×20 ml). The combined organic extracts were washed with brine (50 ml), dried (MgSO4), and solvent evaporated in vacuo to give the subtitled compound as an orange oil which was used in the next step without further purification. MS: ESI (positive): 362, 364 (M+H).
Workup
- customat −78° C.
- temperatureto warm to room temperature
- customThe reaction was quenched with saturated NaHCO3 (20 ml)
- extractionextracted with ethyl acetate (3×20 ml)
- washThe combined organic extracts were washed with brine (50 ml)
- dry with materialdried (MgSO4), and solvent
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-b12e3e10cbf94e50b39668ebc6fc31b8
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08716276B2
Reaction notes
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