Isopropanol → HCID 16756806, compound

HRID 2262337Notes

Reaction equation

HRID 2262337 reaction equation
S(Cl)(Cl)=O.[CH:5]([OH:8])([CH3:7])[CH3:6].[C:9]([NH:22][C@H:23]([C:29](O)=[O:30])[CH2:24][CH2:25][C:26](=[O:28])[NH2:27])(=[O:21])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>O>[CH:5]([O:8][C:29](=[O:30])[C@H:23]([CH2:24][CH2:25][C:26](=[O:28])[NH2:27])[NH:22][C:9](=[O:21])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 24386Thionyl ChlorideHCID 16213882N~2~-Dodecanoyl-L-glutamine

Product 1

HCID 16756806HCID 16756806, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

108 g of L-glutamine was dissolved in 343 g of water and 102 g of aqueous 27% sodium hydroxide solution, and cooled to 10° C. 138 g of acetone was added to it, and 152 g of lauroyl chloride and 108 g of aqueous 27% sodium hydroxide solution were dropwise added thereto. The acylation liquid was diluted with 300 g of water, then neutralized with 35 g of 75% sulfuric acid and filtered to obtain a white powdery substance, N-lauroyl-L-glutamine. 72.4 g of thionyl chloride was dropwise added to 424 g of isopropyl alcohol, then 100 g of N-lauroyl-L-glutamine was added thereto and reacted at room temperature for 8.5 hours. The reaction liquid was added to 2.0 L of water to precipitate the intended product, and this was taken out by filtration to obtain a crude product. This was recrystallized repeatedly three times with acetone to obtain 59.1 g of N-lauroyl-L-glutamine isopropyl ester.

Workup

  1. customreacted at room temperature for 8.5 hours
  2. customThe reaction liquid
  3. customto precipitate the intended product
  4. filtrationthis was taken out by filtration
  5. customto obtain a crude product
  6. customThis was recrystallized repeatedly three times with acetone

Sources & evidence

ORD record
ord-0dfbc301decd47dfa19e832982097f22
Source dataset
uspto-grants-2010_12
Patent number
US07850955B2

Reaction notes

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