Allyl chloroformate → HCID 11196464, compound

HRID 1823642Notes

Reaction equation

HRID 1823642 reaction equation
[NH2:1][C@@:2]1([C:11]([OH:13])=[O:12])[CH2:7][CH2:6][C@@H:5]2[C@H:3]1[C@H:4]2[C:8]([OH:10])=[O:9].O1CCOCC1.Cl[C:21]([O:23][CH2:24][CH:25]=[CH2:26])=[O:22]>C(=O)(O)[O-].[Na+].O>[CH2:24]([O:23][C:21]([NH:1][C@@:2]1([C:11]([OH:13])=[O:12])[CH2:7][CH2:6][C@@H:5]2[C@H:3]1[C@H:4]2[C:8]([OH:10])=[O:9])=[O:22])[CH:25]=[CH2:26]

Participants

6

Reactant 3

HCID 18052Allyl chloroformateHCID 312751,4-DioxaneHCID 213056Eglumegad

Product 1

HCID 11196464HCID 11196464, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

(1S,2S,5R,6S)-2-Amino-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid (15.0 g, 73.9 mmol) was slowly dissolved in 250 mL of saturated sodium bicarbonate. After complete solution, dioxane (100 mL) and allyl chloroformate (15.7 mL, 147.8 mmol) were added at room temperature and the mixture was stirred overnight. The reaction mixture was diluted with water (100 mL) and washed with three portions of ethyl acetate. The organic layer was extracted once with saturated sodium bicarbonate. The combined aqueous layers were acidified to pH 1 with 4N hydrochloric acid and extracted with two portions of ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated to provide the title compound as an oil (13.4 g, 67% yield).

Workup

  1. washwashed with three portions of ethyl acetate
  2. extractionThe organic layer was extracted once with saturated sodium bicarbonate
  3. extractionextracted with two portions of ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ea2200241666465fb9e98748c21262a2
Source dataset
uspto-grants-2006_05
Patent number
US07038077B2

Reaction notes

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