Dodecanoyl chloride → HCID 86759881, compound

HRID 968181Notes

Reaction equation

HRID 968181 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[C:9]([OH:28])(=[O:27])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20]CCCCCC.ON1C(=O)CCC1=O.CCN(C(C)C)C(C)C.C(Cl)(=O)CCCCCCCCCCC>C1COCC1>[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[C:9]([OH:28])(=[O:27])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 8166Dodecanoyl chlorideHCID 80170N-HydroxysuccinimideHCID 81531DiisopropylethylamineHCID 86759882HCID 86759882, compound

Product 1

HCID 86759881HCID 86759881, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

It was prepared exactly in a similar way as in the preparation of oleic acid N-hydroxy succinimide. In brief, 1.33 gr. of N-hydroxy succinimide (11.56 mmole, 1.5 eq.) and DIEA (1.35 ml) were dissolved in 50.0 ml of anhydrous THF and gently stirred at 0° C. under nitrogen atmosphere. Then, Lauroyl chloride (1.8 ml, 99% Sigma, 7.8 mmole, 1.0 eq.) dissolved in 50 ml of anhydrous THF was added dropwise during 1 h. The mixture was gently stirred for 2 h at 0° C. and over-night at room temperature. The resulting precipitate were discarded by filtration and the filtrate was evaporated under reduced pressure, redissolved in small amount of DCM and purified over silica-gel column using DCM as eluent. Fractions containing the product were combined and solvent was removed under reduced pressure. The resulting white solid was dried in vacuum over NaOH-pellets.

Workup

  1. additionwas added dropwise during 1 h
  2. stirringThe mixture was gently stirred for 2 h at 0° C. and over-night at room temperature
  3. filtrationThe resulting precipitate were discarded by filtration
  4. customthe filtrate was evaporated under reduced pressure
  5. dissolutionredissolved in small amount of DCM
  6. custompurified over silica-gel column
  7. additionFractions containing the product
  8. customsolvent was removed under reduced pressure
  9. dry with materialThe resulting white solid was dried in vacuum over NaOH-pellets

Sources & evidence

ORD record
ord-331d805d375047b0a98becbc0f389acc
Source dataset
uspto-grants-2005_10
Patent number
US06958325B2

Reaction notes

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