Ethyl Acetate → (+)-Methyl 5-(3-(hydroxymethyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate

HRID 846449Notes

Reaction equation

HRID 846449 reaction equation
[Si]([O:18][CH2:19][C:20]1[CH:21]=[C:22]([CH:26]([S:34][CH2:35][CH2:36][C:37](=[O:41])[N:38]([CH3:40])[CH3:39])[S:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH:23]=[CH:24][CH:25]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>C1COCC1>[OH:18][CH2:19][C:20]1[CH:21]=[C:22]([CH:26]([S:34][CH2:35][CH2:36][C:37](=[O:41])[N:38]([CH3:40])[CH3:39])[S:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 85324336(+)-Methyl 5-(3-(t-butyldiphenylsilyloxymethyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate

Product 1

HCID 19930508(+)-Methyl 5-(3-(hydroxymethyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (-)-meth-yl 5-(3-(t-butyldiphenylsilyloxymethyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate (step 5) (1.377 g, 2.26 mM) in THF (25 mL) at room temperature was slowly added tetra-n-butylammonium fluoride (1M) in THF (2.34 mL). The solution was stirred 2 hrs at room temperature Ethyl acetate was added to the reaction mixture, and the organic layer it was washed with brine (3x), dried over sodium sulfate, filtered and evaporated to dryness. Purification by flash chromatography using 40% acetone in hexane afforded the title compound.

Workup

  1. customat room temperature
  2. additionwas added to the reaction mixture
  3. washthe organic layer it was washed with brine (3x)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-449f1218d4294442a5963be3edd2641d
Source dataset
uspto-grants-1992_08
Patent number
US05136034

Reaction notes

Loading…