Water → HCID 117997671, compound

HRID 1486686Notes

Reaction equation

HRID 1486686 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@:9]1([C:19]([OH:21])=[O:20])[C@@H:14]([F:15])[CH2:13][C@@H:12]2[C@H:10]1[C@H:11]2[C:16]([OH:18])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(Br)C=C>[C:1]([O:5][C:6]([NH:8][C@@:9]1([C:19]([O:21][CH2:14][CH:9]=[CH2:10])=[O:20])[C@@H:14]([F:15])[CH2:13][C@@H:12]2[C@H:10]1[C@H:11]2[C:16]([O:18][CH2:3][CH:1]=[CH2:2])=[O:17])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 117987602HCID 117987602, compound

Product 1

HCID 117997671HCID 117997671, compoundYield 181.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 7841Allyl bromideSolvent

Procedure

To a solution of (1S,2S,3S,5R,6S)-2-((tert-butoxycarbonyl)amino)-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (D-13-1, 1.30 g) in N,N-dimethylformamide (25 mL), allyl bromide (1.09 mL) and potassium carbonate (1.18 g) were added at room temperature, and the mixture was stirred at the same temperature for 18 hours. To the reaction solution, water was added, and the mixture was extracted three times with ethyl acetate. The combined organic layer was washed three times with 5% saline and once with brine, sequentially. After the organic layer was dried over anhydrous sodium sulfate, the insoluble was filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (silica gel cartridge, hexane:ethyl acetate=100:0-60:40) to give (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) as a colorless oil.

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washThe combined organic layer was washed three times with 5% saline
  3. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  4. filtrationthe insoluble was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (silica gel cartridge, hexane:ethyl acetate=100:0-60:40)

Sources & evidence

ORD record
ord-6d9dc11c6fcf4b41bcc625eb2e2c4112
Source dataset
uspto-grants-2016_08
Patent number
US09428483B2

Reaction notes

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