Acetic Anhydride → Ethyl (3R,4R,5S)-4-acetamido-5-azido-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate
Reaction equation
[NH2:1][C@@H:2]1[C@@H:7]([N:8]=[N+:9]=[N-:10])[CH2:6][C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][C@H:3]1[O:16][CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19].C(N(CC)CC)C.[C:29](OC(=O)C)(=[O:31])[CH3:30]>C(Cl)Cl>[C:29]([NH:1][C@@H:2]1[C@@H:7]([N:8]=[N+:9]=[N-:10])[CH2:6][C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][C@H:3]1[O:16][CH:17]([CH2:18][CH3:19])[CH2:20][CH3:21])(=[O:31])[CH3:30]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
Ethyl (3R,4R,5S)-4-Amino-5-azido-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate (14 gm) was added to triethyl amine (10 gm) and methylene chloride (110 ml) and then the contents were cooled to 20° C. To the contents added acetic anhydride (5.6 gm) at 20-25° C. for 1 hour and then stirred for 3 hours at 20-25° C. The reaction mass was quenched into water (140 ml) and then separated the layers. The organic layer was washed with 8% sodium bicarbonate solution (140 ml) and then washed with 30% sodium chloride solution (140 ml). The organic layer was distilled and recrystallized from n-hexane (70 ml) to give 8.5 gm of Ethyl (3R,4R,5S)-4-(Acetylamino)-5-azido-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate.
Workup
- customThe reaction mass was quenched into water (140 ml)
- customseparated the layers
- washThe organic layer was washed with 8% sodium bicarbonate solution (140 ml)
- washwashed with 30% sodium chloride solution (140 ml)
- distillationThe organic layer was distilled
- customrecrystallized from n-hexane (70 ml)
Sources & evidence
- ORD record
- ord-56bce2c6c51f40a7b38d8e4abac65f87
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687658B2
Reaction notes
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