Hydrogen chloride-ethyl acetate → HCID 131736794, compound
Reaction equation
C(OC([NH:8][C@@:9]1([C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])[C@@H:14]([F:15])[CH2:13][C@@H:12]2[C@H:10]1[C@H:11]2[C:16]([O:18][CH2:19][CH:20]=[CH2:21])=[O:17])=O)(C)(C)C.C(OCC)(=O)C.Cl>>[NH2:8][C@@:9]1([C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])[C@@H:14]([F:15])[CH2:13][C@@H:12]2[C@H:10]1[C@H:11]2[C:16]([O:18][CH2:19][CH:20]=[CH2:21])=[O:17]Participants
Procedure
To (1S,2S,3S,5R,6S)-diallyl 2-((tert-butoxycarbonyl)amino)-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylate (D-13-2, 1.49 g), a 4 mol/L hydrogen chloride-ethyl acetate solution (24 mL) was added at 0° C., and the mixture was stirred at room temperature for 18 hours. The reaction solution was thereafter concentrated under reduced pressure, a saturated aqueous sodium bicarbonate solution was added, and the mixture was extracted three times with ethyl acetate. After the combined organic layer was washed once with brine and dried over anhydrous sodium sulfate, the insoluble was filtered off and the filtrate was concentrated under reduced pressure to give (1S,2S,3S,5R,6S)-diallyl 2-amino-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylate (D-13-3, 949 mg).
Workup
- concentrationThe reaction solution was thereafter concentrated under reduced pressure
- additiona saturated aqueous sodium bicarbonate solution was added
- extractionthe mixture was extracted three times with ethyl acetate
- washAfter the combined organic layer was washed once with brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationthe insoluble was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-cf5666faf56a4febb35a309b956cb8fb
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428483B2
Reaction notes
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