Hydrochloric Acid → HCID 117987534, compound

HRID 1486668Notes

Reaction equation

HRID 1486668 reaction equation
[NH2:1][C@@:2]1([C:12]([OH:14])=[O:13])[C@@H:7]([F:8])[CH2:6][C@@H:5]2[C@H:3]1[C@H:4]2[C:9]([OH:11])=[O:10].C(=O)(O)[O-].[Na+].Cl[C:21]([O:23][CH2:24][CH:25]=[CH2:26])=[O:22].Cl>O1CCOCC1>[CH2:24]([O:23][C:21]([NH:1][C@@:2]1([C:12]([OH:14])=[O:13])[C@@H:7]([F:8])[CH2:6][C@@H:5]2[C@H:3]1[C@H:4]2[C:9]([OH:11])=[O:10])=[O:22])[CH:25]=[CH2:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 18052Allyl chloroformateHCID 516892Sodium BicarbonateHCID 9815616(1S,2S,3S,5R,6S)-2-amino-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid

Product 1

HCID 117987534HCID 117987534, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of (1S,2S,3S,5R,6S)-2-amino-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (IV) (4.00 g) in dioxane (24 mL) and a saturated aqueous sodium bicarbonate solution (48 mL), allyl chloroformate (0.42 mL) was added dropwise over 15 minutes, and the mixture was stirred at room temperature for 20 hours. After addition of 1 mol/L hydrochloric acid to the reaction solution to adjust it to pH 1, the mixture was extracted three times with ethyl acetate. The combined ethyl acetate layer was dried over anhydrous sodium sulfate, the drying agent was filtered off and then the filtrate was concentrated under reduced pressure to give (1S,2S,3S,5R,6S)-2-(((allyloxy)carbonyl)amino)-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (A-1-1, 6.23 g) as a colorless amorphous.

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. dry with materialThe combined ethyl acetate layer was dried over anhydrous sodium sulfate
  3. filtrationthe drying agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ceb21739abc24c1c902a09608e4df5d9
Source dataset
uspto-grants-2016_08
Patent number
US09428483B2

Reaction notes

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