Acetic Acid → HCID 89493860, compound

HRID 711406Notes

Reaction equation

HRID 711406 reaction equation
C(O)(=O)C.C([O-])(=O)C.[Na+].Cl.[NH2:11][C@H:12]([C:18]([O:20][CH3:21])=[O:19])[CH2:13][C:14]([O:16][CH3:17])=[O:15].CO[CH:24]1[CH2:28][CH2:27][CH:26](OC)O1>ClCCl.O>[N:11]1([C@@H:12]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:18]([O:20][CH3:21])=[O:19])[CH:24]=[CH:28][CH:27]=[CH:26]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 790982,5-DimethoxytetrahydrofuranHCID 517045Sodium AcetateHCID 2734892L-Aspartic acid, 1,4-dimethyl ester, hydrochloride (1:1)

Product 1

HCID 89493860HCID 89493860, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Acetic acid (2.5 ml) and sodium acetate (32.5 mmol, 2.6 g) were added to a solution of dimethyl L-aspartate hydrochloride (29.5 mmol, 5.830 g) in dichloromethane (60 ml) and water (30 ml). Tetrahydro-2,5-dimethoxyfuran (29.5 mmol, 3.8 ml) was added to the resulting mixture heated at 80° C. After 90 min. the solution was cooled and the acqueous layer was washed with DCM. The combined organic layers were washed with brine and then dried, filtered and evaporated. The crude residue was purified by chromatograpgy on silica gel (eluent:Hex/AcOEt:7/3) to give the wanted compound as a colorless viscous oil (4.3 g, 68% yield).

Workup

  1. temperatureAfter 90 min. the solution was cooled
  2. washthe acqueous layer was washed with DCM
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude residue was purified by chromatograpgy on silica gel (eluent:Hex/AcOEt:7/3)

Sources & evidence

ORD record
ord-7f8c02f387da44d2ad86b20864fdd757
Source dataset
uspto-grants-2015_11
Patent number
US09181258B2

Reaction notes

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