Methanol → HCID 178501505, compound

HRID 2254596Notes

Reaction equation

HRID 2254596 reaction equation
C(OC([N:8]([S:20]([C:23]1[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=1[CH3:31])(=[O:22])=[O:21])[C:9](=[NH:19])[NH:10][CH2:11][CH2:12][CH2:13][C@@H:14]([C:16]([OH:18])=[O:17])[NH2:15])=O)(C)(C)C.Cl.O1CCOC[CH2:34]1.O=S(Cl)Cl.CO>O1CCOCC1>[NH2:15][C@H:14]([C:16]([O:18][CH3:34])=[O:17])[CH2:13][CH2:12][CH2:11][NH:10][C:9](=[NH:19])[NH:8][S:20]([C:23]1[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=1[CH3:31])(=[O:22])=[O:21]

Participants

6

Reactant 4

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 204431481,4-Dioxane hydrochlorideHCID 178425971HCID 178425971, compound

Product 1

HCID 178501505HCID 178501505, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.10 g of Nω -t-butoxycarbonyl-Nω -mesitylenesulfonyl-L-arginine [Boc-Arg(Mts)-OH] was dissolved in 31 ml of dry dioxane and 31 ml of 4N HCl-dioxane was added thereto. The obtained mixture was stirred at room temperature for 1 hour. The resulting solution was concentrated under reduced pressure to dryness and then crystallized by adding dry ether. The target product was collected by centrifugation, washed with dry ether several times and dried in a desiccator. Thus 1.1 g of HCl.H-Arg(Mts)-OH from which Boc groups had been removed was obtained. This product was next added to a solution, which had been prepared by slowly adding 2.9 ml of SOCl2 to 10.6 ml of methanol and stirring at -10° C. for 10 minutes, and the obtained mixture was stirred for 15 hours, concentrated to dryness, crystallized from dry ether, centrifuged, washed with dry ether several times and dried. Thus 0.94 g of HCl.H-Arg(Mts)-OMe was obtained.

Workup

  1. concentrationThe resulting solution was concentrated under reduced pressure to dryness
  2. customcrystallized
  3. additionby adding dry ether
  4. customThe target product was collected by centrifugation
  5. washwashed with dry ether several times
  6. customdried in a desiccator
  7. customH-Arg(Mts)-OH from which Boc groups had been removed
  8. customwas obtained
  9. additionThis product was next added to a solution, which
  10. customhad been prepared
  11. stirringstirring at -10° C. for 10 minutes
  12. stirringthe obtained mixture was stirred for 15 hours
  13. concentrationconcentrated to dryness
  14. customcrystallized from dry ether
  15. washwashed with dry ether several times
  16. customdried

Sources & evidence

ORD record
ord-07df86cc73ab498c8cefe44d9e5440ef
Source dataset
uspto-grants-1993_08
Patent number
US05236903

Reaction notes

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