Tert-Butylamine → L-Lysine

HRID 971390Notes

Reaction equation

HRID 971390 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:19]([OH:21])=[O:20])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7]C(OCC1C=CC=CC=1Cl)=O.C(N)(C)(C)C.N(C(OC(C)(C)C)=O)[C@H](C(O)=O)CCCCNC(OCC1C=CC=CC=1)=O.C1(NC2CCCCC2)CCCCC1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[NH2:1][C@H:2]([C:19]([OH:21])=[O:20])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]

Participants

7

Reactant 5

HCID 6385Tert-ButylamineHCID 7519AnisoleHCID 7582DicyclohexylamineHCID 2724765Boc-Lys(Z)-OHHCID 7269331Boc-Lys(2-Cl-Z)-OH

Product 1

HCID 5962L-Lysine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Procedure

Relative stability of amino-protecting groups, namely Xys, 2-chlorobenzyloxycarbonyl and Z against trifluoroacetic acid. Boc-Lys(Xys)-OH(41.4 mg, 0.1 m.mol), Boc-Lys(2-Cl-Z)-OH.t-butylamine salt (48.8 mg, 0.1 m.mol) and Boc-Lys(Z)-OH.dicyclohexylamine salt (56.1 mg, 0.1 m.mol) are each dissolved in trifluoroacetic acid (0.5 ml) containing anisole (0.03 ml) and the solutions are allowed to stand at room temperature for 24 hours. The trifluoroacetic acid is distilled off and the residue is made up to 20 ml with cold water. An aliquot of this solution is taken and its lysine content is determined by means of an amino acid analyzer. The yields of lysine (% cleavage of ε-amino-protecting groups) are calculated.

Workup

  1. distillationThe trifluoroacetic acid is distilled off

Sources & evidence

ORD record
ord-3207bc73f47e44cd8501bd459059c654
Source dataset
uspto-grants-1979_07
Patent number
US04159979

Reaction notes

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