Sulfuric Acid → HCID 178443295, compound

HRID 1821537Notes

Reaction equation

HRID 1821537 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:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[OH-].[Na+].S(=O)(=O)(O)O>O.C(O)(C)(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:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8166Dodecanoyl chlorideHCID 14798Sodium Hydroxide2×HCID 178418600HCID 178418600, compound

Product 1

HCID 178443295HCID 178443295, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
12.5 °C

Procedure

L-Arginine (50 g) was added with t-butyl alcohol (315 g) and water (125 g). The reaction mixture was added dropwise with lauroyl chloride (69 g) and 27 wt % aqueous sodium hydroxide (50 g) over 1 hour and 20 minutes, while the system was maintained at 10 to 15° C. and pH 10 to 11. After the addition, the reaction mixture was warmed to 45° C., added with sulfuric acid (17 g) and uniformly dissolved. Then, the system was adjusted to pH 4.9 with further addition of 27 wt % aqueous sodium hydroxide. The deposited crystals were collected by filtration and washed with water to obtain white crystals (92 g, yield: 90%).

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was warmed to 45° C.
  3. dissolutionuniformly dissolved
  4. filtrationThe deposited crystals were collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-1a490147edb0486c9572ec6968be559e
Source dataset
uspto-grants-2009_10
Patent number
US07608250B2

Reaction notes

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