4-Methylmorpholine → L-(-)-Ornithine

HRID 2425064Notes

Reaction equation

HRID 2425064 reaction equation
[NH:1](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:2]([C:19]([OH:21])=[O:20])[CH2:3][CH2:4][CH2:5][NH:6]C(=C1C(=O)CC(C)(C)CC1=O)C.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[NH2:1][C@H:2]([C:19]([OH:21])=[O:20])[CH2:3][CH2:4][CH2:5][NH2:6]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178464025HCID 178464025, compound

Product 1

HCID 6262L-(-)-Ornithine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Fmoc-Orn(Dde)-OH (386 mg, 0.744 mmol, 4 equiv.), HOBt (114 mg, 0.744 mmol, 4 equiv.) and HBTU (282 mg, 0.744 mmol, 4 equiv.) were dissolved in 2.3 ml DMF. This mixture was let stand at room temperature for 10 min before 0.4 M N-methylmorpholine (in DMF) (3.7 ml, 1.488 mmol, 8 equiv.) was added to it. The resin was treated with this new mixture with gentle rocking for ˜3 h. After the solution was filtered away, the resin was washed three times with DMF (5 ml each time).

Workup

  1. customat room temperature
  2. customfor 10 min
  3. additionwas added to it
  4. additionThe resin was treated with this new mixture with gentle rocking for ˜3 h
  5. filtrationAfter the solution was filtered away
  6. washthe resin was washed three times with DMF (5 ml each time)

Sources & evidence

ORD record
ord-885f8c3e498c4bf9aca4d6f5ab8f9351
Source dataset
uspto-grants-2011_06
Patent number
US07964636B2

Reaction notes

Loading…