Thionyl Chloride → 2-Tetradecylhexadecanoyl chloride

HRID 866730Notes

Reaction equation

HRID 866730 reaction equation
[CH2:1]([CH:15]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:16](O)=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].S(Cl)([Cl:35])=O>C1C=CC=CC=1>[CH2:1]([CH:15]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:16]([Cl:35])=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 100040252-tetradecylhexadecanoic Acid

Product 1

HCID 203183022-Tetradecylhexadecanoyl chlorideYield 72.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1.0 g of 2-tetradecylhexadecanoic acid and 0.79 g of thionyl chloride in 5 ml of benzene was refluxed for 7 hours. After removal of benzene and thionyl chloride, anhydrous benzene was added to the residue and then benzene was removed by distillation. This procedure was repeated 3 times to remove thionyl chloride completely. The residue was recrystallized from anhydrous hexane to obtain 0.75 g of 2-tetradecylhexadecanoyl chloride having a melting point of 51°-53° C. To the solution of 0.85 g of 1-α-O-benzyl-N-acetylmuramyl-L-alanyl-D-isoglutamine benzyl ester in 35 ml of anhydrous pyridine, was added 4.9 g of 2-tetradecylhexadecanoyl chloride dissolved in 35 ml of anhydrous tetrahydrofuran at 17°-18° C. After 45 minutes, 20 ml of water was added and the solution was stirred for 35 minutes at room temperature. The solution was adjusted to pH 3 with 1 M hydrochloric acid and extracted with chloroform. The chloroform solution was washed with saturated brine, and dried. After removal of solvent, the residue was subjected to silica gel column chromatography. Eluate with a mixture of chloroform and methanol (20:1) was concentrated and the residue was recrystallized from methanol to obtain 0.75 g of 6-O-(2-tetradecylhexadecanoyl)-1-α-O-benzyl-N-acetylmuramyl-L-alanyl-D-isoglutamine benzyl ester having a melting point of 173°-174° C.

Workup

  1. customAfter removal of benzene and thionyl chloride, anhydrous benzene
  2. additionwas added to the residue
  3. custombenzene was removed by distillation
  4. customto remove thionyl chloride completely
  5. customThe residue was recrystallized from anhydrous hexane

Sources & evidence

ORD record
ord-4bb3110004584ba59d0f5581c7df72ef
Source dataset
uspto-grants-1978_07
Patent number
US04101536

Reaction notes

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