Acetic Acid → HCID 462620, compound

HRID 265321Notes

Reaction equation

HRID 265321 reaction equation
[Si]([O:8][CH2:9][C:10]1[S:11][S:12][C:13]([CH2:16][O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C>C1COCC1>[C:18]([O:17][CH2:16][C:13]1[S:12][S:11][C:10]([CH2:9][OH:8])=[CH:15][CH:14]=1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium Fluoride2×HCID 88379550HCID 88379550, compound

Product 1

HCID 462620HCID 462620, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of the 3-[(tert-butyldimethysilyloxy)methyl]-6-(benzoyloxymethyl)-1,2-dithiin (250 mg, 0.63 mg) obtained above in THF (0.2-0.3M) was added a premixed solution of tetrabutylammonium fluoride (TBAF, 800-1250 mol % of a 1M solution in THF) and acetic acid (1.75-2:1, v/v, 1M TBAF/HOAc) at room temperature. The mixture was stired for 1-4 h. The solvent was concentrated and the residue was partitioned between water (40 mL) and EtOAc (60 mL). The organic phase was washed with dilute aqueous NaHCO3 (50 mL), water (50 mL), dried (Na2SO4), and concentrated to a small volume. Purification was done by chromatography, eluting with EtOAc/hexane mixtures, to yield 94 mg of the title compound (53.4%); 1H NMR (CDCl3) δ8.08-8.05 (m, 2 H), 7.57 (dd, J=7.2, 8.0, 1 H), 7.48-7.39 (m, 2 H), 6.47 (d, J=6.0, 1 H), 6.40 (d, J=6.0, 1 H), 4.96 (s, 2 H), 4.28 (s, 2 H), 2.2 (bs); MS 280.0 (M+).

Workup

  1. concentrationThe solvent was concentrated
  2. customthe residue was partitioned between water (40 mL) and EtOAc (60 mL)
  3. washThe organic phase was washed with dilute aqueous NaHCO3 (50 mL), water (50 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to a small volume
  6. customPurification
  7. washeluting with EtOAc/hexane mixtures

Sources & evidence

ORD record
ord-a0135f0d7c1e414394bab17eeaccac11
Source dataset
uspto-grants-1997_07
Patent number
US05648354

Reaction notes

Loading…