Hydrochloric Acid → HCID 178443184, compound

HRID 488699Notes

Reaction equation

HRID 488699 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:27])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[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:27])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 66986Myristoyl chlorideHCID 178418600HCID 178418600, compound

Product 1

HCID 178443184HCID 178443184, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

As in Synthetic Example 1, to 113 g of L-arginine were added 706 g of isopropyl alcohol and 302 g of water. Thereto were concurrently added dropwise 176 g of myristoyl chloride (manufactured by Nippon Oil and Fats Co., Ltd.) and 27 wt % NaOH aqueous solution over a period of 2 hours with the pH being maintained at 10.5 to 11.5 and the reaction temperature, at 10 to 13° C. After 1 hour of aging, the reaction mixture was warmed to 50° C. and adjusted to below pH 2.7 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 1,500 g of water and 492 g of isopropyl alcohol, successively. The resulting washed crystals were dried under reduced pressure to obtain 230 g of mono-Nα-myristoyl-L-arginine as flake-shaped crystals (yield 92.2%).

Workup

  1. temperaturebeing maintained at 10.5 to 11.5
  2. customat 10 to 13° C
  3. dissolutionto dissolve the reaction product completely
  4. customto precipitate crystals
  5. temperaturethe resulting slurry was gradually cooled to 10° C.
  6. temperatureWhen the slurry was cooled to 10° C.
  7. filtrationthe crystals were collected by filtration
  8. washwashed with 1,500 g of water and 492 g of isopropyl alcohol
  9. washThe resulting washed crystals
  10. customwere dried under reduced pressure

Sources & evidence

ORD record
ord-48afb1171d9a420fa2c050350362d7b3
Source dataset
uspto-grants-2005_12
Patent number
US06974582B2

Reaction notes

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