Triethylamine → HCID 59299352, compound

HRID 2235256Notes

Reaction equation

HRID 2235256 reaction equation
[CH:1]1([NH:7][C:8](=[O:16])[CH:9]([OH:15])[C:10]([CH3:14])([CH3:13])[CH2:11]O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N([CH2:22][CH3:23])CC)C.[C:24]1(C)[C:25]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:27]=C[CH:29]=1.[H-].[Na+]>C(Cl)Cl>[CH:1]1([N:7]2[CH2:11][C:10]([CH3:14])([CH3:13])[CH:9]([O:15][S:30]([C:25]3[CH:26]=[CH:27][C:22]([CH3:23])=[CH:29][CH:24]=3)(=[O:32])=[O:31])[C:8]2=[O:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 289865HCID 289865, compound

Product 1

HCID 59299352HCID 59299352, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Place N-cyclohexyl-2,4-dihydroxy-3,3-dimethyl-butyramide (2.178 g, 9.51 mmol), triethylamine (2.7 ml, 19.31 mmol) and toluenesulfonyl chloride (3.70 g, 19.21 mmol) in CH2Cl2 (50 mL) at 0° C. Stir for 30 minutes at 0° C. Quench with hexane and warm to room temperature. Filter white precipitate. Strip the solvent and dissolve the residue in 40 ml of dry THF under the nitrogen atmosphere. Add sodium hydride (3.4 g, 85 mmol) and stir at room temperature for 12 hours. Quench the reaction with methanol/water mixture. Extract with ethyl acetate. Wash the extract with brine and dry over magnesium sulfate. Purification by flash chromatography affords 1.25 g (36%) of the title compound: Mass spectrum (apci) m/z=366 (M+H).

Workup

  1. customat 0° C
  2. customQuench with hexane
  3. temperaturewarm to room temperature
  4. filtrationFilter white precipitate
  5. dissolutionStrip the solvent and dissolve the residue in 40 ml of dry THF under the nitrogen atmosphere
  6. customQuench
  7. customthe reaction with methanol/water mixture
  8. extractionExtract with ethyl acetate
  9. washWash the
  10. extractionextract with brine
  11. dry with materialdry over magnesium sulfate
  12. customPurification by flash chromatography

Sources & evidence

ORD record
ord-a2458d88773e4e84a76641c9464a3622
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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