L-Lysine → Ninhydrin

HRID 1063512

Reaction equation

N[C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6]N.N(C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H]([C:20](O)=[O:21])CC1C=CC=CC=1.C(N=C=N[CH:46]([CH3:48])C)(C)C.C(Cl)Cl.CN(C=[O:56])C>>[CH:48]1[CH:46]=[C:3]2[C:2]([C:8]([OH:10])([OH:9])[C:20](=[O:21])[C:4]2=[CH:5][CH:6]=1)=[O:56]

Participants

Reactant 4

HCID 5962L-Lysine

HCID 12734Diisopropylcarbodiimide

HCID 978331Fmoc-phenylalanine

HCID 22350042dichloromethane N,N-dimethylformamide

Product 1

HCID 10236Ninhydrin

Procedure

To the deprotected Lys-resin sample was added Fmoc-Phe (8.8 mg, 33.2 μmol) in DCM/DMF and 1,3-diisopropylcarbodiimide (DIC) (3 μL, 20 μmol). The coupling reaction was continued for 2 h and ninhydrin tests gave negative amino group readings. The Fmoc-Phe-Lys(ivDde) on resin was then treated with photogenerated piperidine as described above. Upon completion of the reaction, the resin was washed with DCM/DMF. Capping of the NH2-Phe-Lys(ivDde)-resin was carried out for 1 h with acetic anhydride (470 μL, 5 mmol) and TEA (700 μL, 5 μmmol) in 1.5 mL DMF to give Ac-Phe-Lys(ivDde)-resin.

Workup

customThe coupling reaction

Sources & evidence

ORD record: ord-089c351e375a4dfb97029e8dd69b41a4
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06965040B1

Linked notes

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