Hydrochloric Acid → HCID 22033370, compound

HRID 1792317Notes

Reaction equation

HRID 1792317 reaction equation
COC[O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][S:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH3:42])[C:10]([C:16]3[CH:21]=[CH:20][C:19]([O:22]COC)=[CH:18][CH:17]=3)([CH3:15])[CH2:11][S:12]2)=[CH:7][CH:6]=1.Cl.O>C(O)(C)C.O1CCCC1>[OH:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][S:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH3:42])[C:10]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)([CH3:15])[CH2:11][S:12]2)=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 22033103HCID 22033103, compound

Product 1

HCID 22033370HCID 22033370, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methyl-4-{9-[2-(2-methoxyethoxy)ethylthio]nonyl}thiochroman (68 mg, 0.109 mmol) in isopropanol (5.5 ml) and tetrahydrofuran (0.9 ml) was added 5N-HCl (1.47 ml) at room temperature, which was stirred for 2 days. Water was added thereto, and the resulting solution was extracted with ethyl acetate. Then, the organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to flash chromatography on silica gel (n-hexane:ethyl acetate=1:1) to give the title compound (43 mg, yield 74%) as a white solid.

Workup

  1. extractionthe resulting solution was extracted with ethyl acetate
  2. washThen, the organic layer was washed with water and saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-80c17f7a2bde4c4eb9e2b31ac6f0ab0f
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

Loading…