Hydrogen fluoride anisole → L-(-)-Ornithine

HRID 1655832Notes

Reaction equation

HRID 1655832 reaction equation
C1(OC)C=CC=CC=1.F.[NH2:10][C@H:11]([C:22]([OH:24])=[O:23])[CH2:12][CH2:13][CH2:14][NH:15]C(=N)N[N+]([O-])=O>>[NH2:10][C@H:11]([C:22]([OH:24])=[O:23])[CH2:12][CH2:13][CH2:14][NH2:15]

Participants

3

Reactant 2

HCID 67368618Hydrogen fluoride anisoleHCID 178512188HCID 178512188, compound

Product 1

HCID 6262L-(-)-Ornithine

Procedure

On this basis Suzuki et al. first carried out a solid-phase synthesis, in which a Boc-Asp(ONb)-Ser(Bzl)-Asp(ONb)-Pro-Arg(NO2) resin was produced stepwise from Boc-Arg(NO2)-OH, which was esterified to a chloromethylated styrene-copolymer resin, coupling with Boc-Asp-(ONb)-OH being performed in the last step. The resin was treated in traditional manner with a hydrogen fluoride anisole mixture, and the crude peptide obtained was hydrogenated for 7 hours to remove the (ONb) groups from Asp in the presence of Pd-on-carbon in water. Product was obtained in a yield of 22% calculated on Boc-Arg(NO2) resin used. Suzuki has not described analysis of side products, but it is well known that hydrogenation of Arg(NO2) gives rise to formation of ornithine, which it is difficult to remove.

Workup

  1. customthe crude peptide obtained
  2. customto remove the (ONb) groups from Asp in the presence of Pd-on-carbon in water
  3. customProduct was obtained in a yield of 22%

Sources & evidence

ORD record
ord-53f385a2e900451fbafcad3d69ffb244
Source dataset
uspto-grants-1993_10
Patent number
US05252464

Reaction notes

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