Stearoyl chloride → HCID 86589699, compound

HRID 600176Notes

Reaction equation

HRID 600176 reaction equation
[C:1](Cl)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(N(CC)CC)C.[C:28]([O:32][C:33](=[O:36])[NH:34][NH2:35])([CH3:31])([CH3:30])[CH3:29]>C1COCC1>[C:28]([O:32][C:33](=[O:36])[NH:34][NH2:35])([CH3:31])([CH3:30])[CH3:29].[C:1]([OH:19])(=[O:32])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 8212Stearoyl chlorideHCID 8471TriethylamineHCID 70091tert-Butyl carbazate

Product 1

HCID 86589699HCID 86589699, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6.06 g (20 mmol) stearic acid chloride is dissolved in 10 ml dry THF. 2.77 ml (20 mmol) triethylamine and 2.91 g (22 mmol) tert-butylcarbazate, dissolved in 10 ml THF, are added dropwise with stirring at room temperature over a 10 min period, and the mixture is stirred for 30 min. The reaction mixture is filtered and the solvent is removed under vacuum. The oily residue is taken up in 50 ml ethyl acetate and extracted twice with 70 ml H2O. The organic phase is dried over Na2SO4 and filtered, and the solvent is evaporated under vacuum. The oily residue is dissolved in 50 ml warm ethanol and stored for 12 h at +4° C. The white precipitate is filtered and washed twice with 30 ml ethanol each. After drying under high vacuum, 3.6 g stearic acid tert-butylcarbazate is obtained; Rf=0.9 (ethyl acetate/n-hexane 2/1).

Workup

  1. additionare added dropwise
  2. stirringthe mixture is stirred for 30 min
  3. filtrationThe reaction mixture is filtered
  4. customthe solvent is removed under vacuum
  5. extractionextracted twice with 70 ml H2O
  6. dry with materialThe organic phase is dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent is evaporated under vacuum
  9. dissolutionThe oily residue is dissolved in 50 ml
  10. temperaturewarm ethanol
  11. waitstored for 12 h at +4° C
  12. filtrationThe white precipitate is filtered
  13. washwashed twice with 30 ml ethanol each
  14. customAfter drying under high vacuum

Sources & evidence

ORD record
ord-9054e143e56f4a38b27e814ee31b0130
Source dataset
uspto-grants-2011_03
Patent number
US07902144B2

Reaction notes

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