Triethylamine → 1-[({[(3R)-2-oxotetrahydro-3-furanyl]oxy}carbonyl)oxy]-2,5-pyrrolidinedione

HRID 643065Notes

Reaction equation

HRID 643065 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][O:5][C:3]1=[O:4].C(N(CC)CC)C.[C:15](=O)([O:24]N1C(=O)CCC1=O)[O:16][N:17]1[C:21](=[O:22])[CH2:20][CH2:19][C:18]1=[O:23]>C(#N)C>[O:4]=[C:3]1[C@H:2]([O:1][C:15]([O:16][N:17]2[C:21](=[O:22])[CH2:20][CH2:19][C:18]2=[O:23])=[O:24])[CH2:7][CH2:6][O:5]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 676246Di(succinimido) carbonateHCID 71570702-Hydroxy-gamma-butyrolactone, (2R)-

Product 1

HCID 865997311-[({[(3R)-2-oxotetrahydro-3-furanyl]oxy}carbonyl)oxy]-2,5-pyrrolidinedione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(R)-alpha-Hydroxybutyrolactone (8 μL, 0.11 mmol) was dissolved in acetonitrile (0.5 mL) and treated with triethylamine (45 μL, 1.5 equivalents), and disuccinimidyl carbonate (42 mg, 1.5 equivalent) at 25° C. for 16 hrs. The solvents were evaporated and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate, the organic layer was separated, washed with brine, dried over magnesium sulfate, filtered and evaporated.

Workup

  1. customThe solvents were evaporated
  2. customthe residue was partitioned between ethyl acetate and saturated sodium bicarbonate
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-8490a168d1f34a86a9f43601e2a11c3d
Source dataset
uspto-grants-2010_04
Patent number
US07696226B2

Reaction notes

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