Hydrochloric Acid → N-Palmitoylglycine

HRID 1464856Notes

Reaction equation

HRID 1464856 reaction equation
[C:1]([O:18]N1C(=O)CCC1=O)(=O)[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][CH3:16].[NH2:26][CH2:27][C:28]([OH:30])=[O:29].C(N(CC)CC)C.Cl>CN(C=O)C.O>[NH:26]([C:1]([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][CH3:16])=[O:18])[CH2:27][C:28]([OH:30])=[O:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 8471TriethylamineHCID 4620598Palmitic acid N-hydroxysuccinimide

Product 1

HCID 151008N-PalmitoylglycineYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

260.3 g of the N-palmitoyloxy-succinimide synthesized above as a whole was suspended in 750 ml of DMF and, to the resultant solution while cooled with ice with stirring, 56.3 g (0.750 mol) of Gly and 83.2 mL (0.598 mol) of triethylamine dissolved in 250 ml of water were added dropwise. The resultant solution was stirred for another 30 minutes while cooled with ice and for another 15 hours during which the resultant solution gradually reached room temperature. To an aqueous solution obtained by dissolving 100 mL of 6 N hydrochloric acid in 1 L of water and adjusting the pH to pH 3, while cooled with ice with stirring, the reaction solution was added dropwise to precipitate a solid, which was filtered off. The resultant product was washed with 2 L of water and then with 1 L of hexane, and was then collected to obtain 114 g (67%) of a desired compound.

Workup

  1. temperaturewhile cooled with ice
  2. additionwere added dropwise
  3. customTo an aqueous solution obtained
  4. temperaturewhile cooled with ice
  5. stirringwith stirring
  6. additionthe reaction solution was added dropwise
  7. customto precipitate a solid, which
  8. filtrationwas filtered off
  9. washThe resultant product was washed with 2 L of water
  10. customwith 1 L of hexane, and was then collected

Sources & evidence

ORD record
ord-9afacb27f2cf49fc8f591ed72138b011
Source dataset
uspto-grants-2015_04
Patent number
US08999300B2

Reaction notes

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