Tert-Butylamine → L-Lysine

HRID 971391Notes

Reaction equation

HRID 971391 reaction equation
C(S([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:18]([OH:20])=[O:19])[NH2:17])(=O)=O)C1C=CC=CC=1.CC(OC(N[C@H](C(O)=O)CCCCNC(OCC1C(Cl)=CC=CC=1)=O)=O)(C)C.C(N)(C)(C)C.F.C1(OC)C=CC=CC=1>>[NH2:17][C@H:16]([C:18]([OH:20])=[O:19])[CH2:15][CH2:14][CH2:13][CH2:12][NH2:11]

Participants

6

Reactant 5

HCID 6385Tert-ButylamineHCID 7519AnisoleHCID 14917Hydrofluoric AcidHCID 7269331Boc-Lys(2-Cl-Z)-OHHCID 66691825Nepsilon-benzylsulfonyllysine

Product 1

HCID 5962L-Lysine

Procedure

Boc-Lys(Xys)-OH (124.4 mg, 0.3 m.mol), Nε -benzylsulfonyllysine (90 mg., 0.3 m.mol) and Boc-Lys-(2-Cl-Z)-OH.t-butylamine salt (146.4 mg, 0.3 m.mol) are each treated with hydrogen fluoride (2 ml) in the presence of anisole (0.1 ml) at -20° C. for one hour. After the hydrogen fluoride is distilled off, the residue is dissolved in water (50 ml). An aliquot of the solution is taken and the lysine content of the sample is determined by an amino acid analyzer. The % yields of lysine are calculated.

Workup

  1. distillationAfter the hydrogen fluoride is distilled off
  2. dissolutionthe residue is dissolved in water (50 ml)

Sources & evidence

ORD record
ord-35d78f11400440878e885d7f4afe6555
Source dataset
uspto-grants-1979_07
Patent number
US04159979

Reaction notes

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