Hydrochloric Acid → (2S)-5-oxooxolane-2-carboxylic acid

HRID 60736

Reaction equation

HRID 60736 reaction equation
N[C@@H:2]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[C:3]([OH:5])=[O:4].Cl.N([O-])=O.[Na+]>O>[O:4]=[C:3]1[O:5][C@H:7]([C:8]([OH:10])=[O:9])[CH2:6][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 33032L-Glutamic AcidHCID 23668193Sodium Nitrite

Product 1

HCID 636468(2S)-5-oxooxolane-2-carboxylic acidYield 63.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of (S)-2-aminopentanedioic acid (100 g, 680 mmol) in H2O (500 mL) was added HCl (140 mL, 1.6 mol) and then NaNO2 (70.4 g, 1.02 mol) in H2O (100 mL) was added slowly at −5° C.-0° C., and the reaction mixture was stirred at room temperature for 24 hours. The solvent was concentrated in vacuo below 50° C. The residue was suspended in EtOAc (500 mL) and filtered. The filtrate was dried over Na2SO4 and concentrated in vacuo to afford 56 g crude product of (2S)-5-oxotetrahydrofuran-2-carboxylic acid (compound 28a) as yellow oil, which was used in next step without further purification.

Workup

  1. concentrationThe solvent was concentrated in vacuo below 50° C
  2. filtrationfiltered
  3. dry with materialThe filtrate was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7d6da0dadc8841038a667aa9079986f3
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Linked notes

Loading…