Potassium Carbonate → HCID 178438920, compound

HRID 2293621Notes

Reaction equation

HRID 2293621 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([O-])([O-])=O.[K+].[K+].[CH3:19][C:20]([C:28]1[CH:29]=[C:30]([S:34](Cl)(=[O:36])=[O:35])[CH:31]=[CH:32][CH:33]=1)([CH3:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O.O1CCOCC1>[CH3:27][C:20]([C:28]1[CH:29]=[C:30]([S:34]([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:35])=[O:36])[CH:31]=[CH:32][CH:33]=1)([CH3:19])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10637600HCID 10637600, compoundHCID 178418600HCID 178418600, compound

Product 1

HCID 178438920HCID 178438920, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

(S)-Arginine (12.6 g) and K2CO3 (12.03 g) are suspended in 50% water/dioxan (250 ml) with vigorous stirring and the reaction mixture is cooled to <5° C. 3-(α,α-Dimethylbenzyl)benzenesulphonyl chloride (21.4g) is added in 6 portions over 30 minutes at <5° C. The mixture is stirred at 20° C. for 2 hours. A colourless solid precipitates. The dioxan is removed by evaporation and the aqueous residue is acidified with cone. HCl. The mixture is extracted with ethyl acetate (3×50ml) and the aqueous phase and all solid materials are combined and neutralised (4M NaOH). The suspension is stirred for 16 hours at 20° C. The solid precipitate is collected by filtration and stirred for 16 hours with a little water. The solid is collected by filtration and dried (NaOH pellets) to give Nα -(3-(α,α-dimethylbenzyl)benzenesulphonyl)-(S)-arginine, m.p. 122°-124° C. (Found: C, 53.49; H, 6.81; N, 11.92; S, 6.93. C21H28N4O4S.2.3H2O requires C, 53.22; H, 6.93; N, 11.82; S, 6.77%).

Workup

  1. temperaturethe reaction mixture is cooled to <5° C
  2. stirringThe mixture is stirred at 20° C. for 2 hours
  3. customA colourless solid precipitates
  4. customThe dioxan is removed by evaporation
  5. extractionThe mixture is extracted with ethyl acetate (3×50ml)
  6. stirringThe suspension is stirred for 16 hours at 20° C
  7. filtrationThe solid precipitate is collected by filtration
  8. stirringstirred for 16 hours with a little water
  9. filtrationThe solid is collected by filtration
  10. dry with materialdried (NaOH pellets)

Sources & evidence

ORD record
ord-c093f3709b4e4fb6bef2ad6db64bec86
Source dataset
uspto-grants-1997_11
Patent number
US05686564

Reaction notes

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