Allyl Alcohol → HCID 117987603, compound
Reaction equation
[CH2:1]([O:4][C:5]([NH:7][C@@:8]1([C:18]([OH:20])=[O:19])[C@@H:13]([F:14])[CH2:12][C@@H:11]2[C@H:9]1[C@H:10]2[C:15]([OH:17])=[O:16])=[O:6])[CH:2]=[CH2:3].[CH2:21](O)[CH:22]=[CH2:23].C(N(CC)C(C)C)(C)C.Cl.C(N=C=NCCCN(C)C)C>C(Cl)(Cl)Cl>[CH2:23]([O:16][C:15]([C@@H:10]1[C@@H:9]2[C@H:11]1[CH2:12][C@H:13]([F:14])[C@@:8]2([NH:7][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[C:18]([OH:20])=[O:19])=[O:17])[CH:22]=[CH2:21]Participants
Conditions
- Temperature
- 0 °C
Procedure
A solution of a mixture of (1S,2S,3S,5R,6S)-2-(((allyloxy)carbonyl)amino)-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (A-1-1, 1.41 g), allyl alcohol (336 μL), N,N-diisopropylethylamine (837 μL) and N,N-dimethylaminopyridine (60 mg) in chloroform (30 mL) was cooled to 0° C. To this solution, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (837 mg) was added, and then the mixture was heated to room temperature and stirred for 2 days. To the reaction solution, chloroform was added, and the organic layer was washed twice with 0.25 mol/L hydrochloric acid, once with water, and once with brine, sequentially. After the organic layer was dried over anhydrous magnesium sulfate, the insoluble was filtered and the filtrate was concentrated under reduced pressure to give (1S,2S,3S,5R,6S)-6-((allyloxy)carbonyl) 2-(((allyloxy)carbonyl)amino)-3-fluorobicyclo[3.1.0]hexane-2-carboxylic acid (B-1-1, 1.30 g) as a colorless amorphous.
Workup
- temperaturethe mixture was heated to room temperature
- washthe organic layer was washed twice with 0.25 mol/L hydrochloric acid, once with water
- dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
- filtrationthe insoluble was filtered
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-1cd6eb412cff421ba2cdbadfd500d5a9
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428483B2
Reaction notes
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