Acetic Anhydride → 3-(tert-Butoxycarbonylamino)-1-(2-phenyl-1,3-dithiaN-2-yl)cyclohexyl acetate
Reaction equation
[C:1]1([CH:7]2[S:12][CH2:11][CH2:10][CH2:9][S:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N-]C(C)C)(C)C.[Li+].C1C[O:24][CH2:23][CH2:22]1.CCCCCCC.C(C1C=CC=CC=1)C.[O:41]=[C:42]1[CH2:47][CH2:46][CH2:45][CH:44]([NH:48][C:49](=[O:55])[O:50][C:51]([CH3:54])([CH3:53])[CH3:52])[CH2:43]1.C(OC(=O)C)(=O)C>C1COCC1.O>[C:23]([O:41][C:42]1([C:7]2([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[S:8][CH2:9][CH2:10][CH2:11][S:12]2)[CH2:47][CH2:46][CH2:45][CH:44]([NH:48][C:49]([O:50][C:51]([CH3:52])([CH3:54])[CH3:53])=[O:55])[CH2:43]1)(=[O:24])[CH3:22]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -20 °C
Procedure
To a solution of 2-phenyl-1,3-dithiane (12 mmol, 2.35 g) in THF (15 mL) at −78° C. was added a solution of lithium diisopropylamide in THF/heptane/ethylbenzene (12 mmol, 1.8 M, 6.7 mL) under argon. The reaction mixture was warmed up to −20° C. and stirred for 30 minutes at −20° C. The reaction mixture was cooled down to −78° C. tert-Butyl 3-oxocyclohexylcarbamate (5 mmol, 1.065 g) in THF was added. The reaction mixture was allowed to warm up to room temperature and stirred for overnight. Acetic anhydride (20 mmol, 1.9 mL) was added. The reaction mixture was stirred at room temperature for 4 hours. Water was added. The organics were extracted with EtOAc. 3-(tert-Butoxycarbonylamino)-1-(2-phenyl-1,3-dithiaN-2-yl)cyclohexyl acetate was obtained after purification by silica gel column chromatography.
Workup
- additionwas added
- temperatureto warm up to room temperature
- stirringstirred for overnight
- stirringThe reaction mixture was stirred at room temperature for 4 hours
- extractionThe organics were extracted with EtOAc
Sources & evidence
- ORD record
- ord-ff08b2de137f4f59a526e402c0e04998
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09351965B2
Reaction notes
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