Hydrochloric Acid → HCID 22857991, compound

HRID 2260425Notes

Reaction equation

HRID 2260425 reaction equation
[H-].[Na+].[CH3:3][C:4]([C:7]1[CH:8]=[C:9]([S:17][C@@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]2[OH:24])[CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)([CH3:6])[CH3:5].[Na+].Cl[CH2:27][C:28]([O-:30])=[O:29].Cl>O1CCCC1.O>[CH3:16][C:13]([C:11]1[CH:10]=[C:9]([S:17][C@@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]2[O:24][CH2:27][C:28]([OH:30])=[O:29])[CH:8]=[C:7]([C:4]([CH3:3])([CH3:5])[CH3:6])[CH:12]=1)([CH3:14])[CH3:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 22858010HCID 22858010, compoundHCID 23665759Sodium chloroacetate

Product 1

HCID 22857991HCID 22857991, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.33 g, 0.0138 mole) was added to a solution of trans-2-[[3,5-bis(1,1-dimethylethyl)phenyl]thio]cyclohexanol (3.4 g, 0.0106 mole) in tetrahydrofuran (50 ml) at 0° C. After stirring the reaction mixture for 1.5 hours, the tetrahydrofuran was removed by rotary evaporation. Dimethyl sulfoxide (75 ml) was added followed by chloroacetic acid sodium salt (1.48 g, 0.0127 mole), and the reaction mixture was stirred at room temperature for 10 days. Water (100 ml) was added dropwise to the mixture followed by 10% hydrochloric acid (10 ml). The product was extracted twice with 200 ml of ethyl acetate. The combined ethyl acetate extracts were washed twice with 200 ml of water, dried over anhydrous sodium sulfate, filtered, and concentrated. The product was purified by chromatography on silica gel. The structure was supported by NMR and elemental analysis (378.6+1/4 mole H2O).

Workup

  1. customthe tetrahydrofuran was removed by rotary evaporation
  2. additionDimethyl sulfoxide (75 ml) was added
  3. stirringthe reaction mixture was stirred at room temperature for 10 days
  4. extractionThe product was extracted twice with 200 ml of ethyl acetate
  5. washThe combined ethyl acetate extracts were washed twice with 200 ml of water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-034554a6b358440fb34a26fa5d22ef1e
Source dataset
uspto-grants-1995_12
Patent number
US05476944

Reaction notes

Loading…