Hydrochloric Acid → HCID 178443080, compound

HRID 488700Notes

Reaction equation

HRID 488700 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].[C:13](Cl)(=[O:29])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].[OH-].[Na+].Cl>O.C(O)(C)C>[C:13]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9])(=[O:29])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8206Palmitoyl chlorideHCID 14798Sodium Hydroxide2×HCID 178418600HCID 178418600, compound

Product 1

HCID 178443080HCID 178443080, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

As in Synthetic Example 1, to 84.7 g of L-arginine were added 706 g of isopropyl alcohol and 302 g of water. Thereto were concurrently added dropwise 147 g of palmitoyl chloride (manufactured by Aldrich) and 27 wt % NaOH aqueous solution over a period of 2 hours with the pH being at 10.5 to 11.5 and the reaction temperature, at 27 to 30° C. After 1 hour of aging, the reaction mixture was warmed to 50° C. and adjusted to below pH 1.8 by adding concentrated hydrochloric acid to dissolve the reaction product completely. Thereafter, the pH was adjusted to 6.0 by adding 27 wt % NaOH aqueous solution to precipitate crystals and the resulting slurry was gradually cooled to 10° C. with stirring. When the slurry was cooled to 10° C., the crystals were collected by filtration and washed with 1,200 g of water and 320 g of isopropyl alcohol, successively. The resulting washed crystals were dried under reduced pressure to obtain 190 g of mono-Nα-palmitoyl-L-arginine as flake-shaped crystals (yield 94.7%).

Workup

  1. customat 27 to 30° C
  2. dissolutionto dissolve the reaction product completely
  3. customto precipitate crystals
  4. temperaturethe resulting slurry was gradually cooled to 10° C.
  5. temperatureWhen the slurry was cooled to 10° C.
  6. filtrationthe crystals were collected by filtration
  7. washwashed with 1,200 g of water and 320 g of isopropyl alcohol
  8. washThe resulting washed crystals
  9. customwere dried under reduced pressure

Sources & evidence

ORD record
ord-b33a88bffd034e08b3c987a7a2a7d63c
Source dataset
uspto-grants-2005_12
Patent number
US06974582B2

Reaction notes

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