Methanesulfonic Acid → L-(-)-Ornithine

HRID 503219Notes

Reaction equation

HRID 503219 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:14]([OH:16])=[O:15])[CH2:3][CH2:4][CH2:5][NH:6]C(OC(C)(C)C)=O.S(O)(C)(=O)=O>CCOC(C)=O>[NH2:1][C@H:2]([C:14]([OH:16])=[O:15])[CH2:3][CH2:4][CH2:5][NH2:6]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 7015803Boc-orn(boc)-OH

Product 1

HCID 6262L-(-)-OrnithineYield 222%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Boc-Orn(Boc)-Amp (1.35 g, 3 mmol) was dissolved in EtOAc (200 ml) and to the slightly cloudy solution was added MsOH (0.43 ml, 6.6 mmol) drop wise. The reaction mixture became a clear solution which was stirred at room temperature for approximately 20 hrs. Solvent was removed and the residue was triturated in hexanes. Off-white solid product was formed which was filtered under vacuum and washed with hexanes. The solid was dried in vacuum oven for 20 hrs to obtain 0.88 g of Orn-Amp-2MsOH (l-ornithine-d-amphetamine dimesylate).

Workup

  1. customSolvent was removed
  2. customthe residue was triturated in hexanes
  3. customOff-white solid product was formed which
  4. filtrationwas filtered under vacuum
  5. washwashed with hexanes
  6. customThe solid was dried in vacuum oven for 20 hrs

Sources & evidence

ORD record
ord-97f334a47bd94ab88c5a10061431f64e
Source dataset
uspto-grants-2010_08
Patent number
US07776917B2

Reaction notes

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