Methyl Acetate → HCID 67314184, compound
Reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:11]([O:14][CH3:15])(=[O:13])[CH3:12].[CH:16]1(/[CH:19]=[N:20]/[S@@:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22])[CH2:18][CH2:17]1.C1C[O:30][CH2:29][CH2:28]1>CCOC(C)=O>[CH:16]1([C@@H:19]([NH:20][S@@:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22])[CH2:28][C:29](=[O:30])[CH2:12][C:11]([O:14][CH3:15])=[O:13])[CH2:17][CH2:18]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
NaHMDS (428 mL, 1 M in hexane) was dissolved in THF (356 mL) and the resulting solution was cooled to −78° C. Methyl acetate (28.3 mL, 356 mmol) was added over 15 minutes and the reaction mixture was stirred at −78° C. for 1 h after which a solution (R,E)-N-(cyclopropylmethylene)-2-methylpropane-2-sulfinamide (26) (12.3 g, 71.3 mmol) in THF (50 mL) was added over 15 minutes. The reaction mixture was warmed to −20° C. and stirred at this temperature for 3 h after which HPLC indicated that the reaction was complete. The resulting solution was diluted with EtOAc (400 mL) and washed with sat. aq. NaHCO3 (200 mL). The organic phase was dried (Na2SO4), filtered, concentrated under vacuum and purified on a silica gel column (eluant hexane/EtOAc, 9/1 to 1/1 to give 16.3 g (79%) of (5S)-methyl 5-cyclopropyl-5-[(R)-1,1-dimethylethylsulfinamido]-3-oxopentanoate (27). Retention time (min)=1.397 method [1], MS (m/z) 290.2 (M+H)+.
Workup
- additionwas added over 15 minutes
- temperatureThe reaction mixture was warmed to −20° C.
- washwashed with sat. aq. NaHCO3 (200 mL)
- dry with materialThe organic phase was dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under vacuum
- custompurified on a silica gel column (eluant hexane/EtOAc, 9/1 to 1/1
Sources & evidence
- ORD record
- ord-ed44857a517c493b9f523009e1831295
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977368B2
Reaction notes
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