Acetic Acid → HCID 54444915, compound

HRID 358105Notes

Reaction equation

HRID 358105 reaction equation
[O:1]1[CH2:5][CH2:4]OC1.[OH2:6].O.[F-].C([N+:11]([CH2:16][CH3:17])([CH2:14][CH3:15])CC)C.[C:18]([OH:21])(=[O:20])C.[O:22]1C[CH2:25][CH2:24][CH2:23]1>C(OCC)(=O)C>[CH3:25][C:24]1([CH:17]2[CH:14]([CH2:15][C:5](=[O:1])[CH3:4])[NH:11][C:16]2=[O:6])[CH2:23][O:22][C:18](=[O:20])[O:21]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 125861,3-DioxolaneHCID 2776564Tetraethylammonium fluoride dihydrate

Product 1

HCID 54444915HCID 54444915, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Dioxolane (B-5)(1.62 g), tetraethylammonium fluoride dihydrate (1.38 g) and acetic acid (0.5 ml) in tetrahydrofuran (10 ml) is stirred at room temperature for 2 hours. The reaction mixture is diluted with ethyl acetate (50 ml), washed with saturated saline, dried and concentrated. The residue purified by silica gel chromatography to give tilted Lactam (C-5)(895 mg) from the fractions eluted with benzene-ethyl acetate (1:5).

Workup

  1. washwashed with saturated saline
  2. customdried
  3. concentrationconcentrated
  4. customThe residue purified by silica gel chromatography
  5. customto give
  6. washeluted with benzene-ethyl acetate (1:5)

Sources & evidence

ORD record
ord-afb75086f65b4359ba25029274e5edbe
Source dataset
uspto-grants-1984_08
Patent number
US04464299

Reaction notes

Loading…