Trifluoroacetic acid → L-Glutamic Acid

HRID 1434503

Reaction equation

HRID 1434503 reaction equation
[NH2:1][C@H:2]([C:12]([O:14]C(C)(C)C)=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6]C(C)(C)C.C(ON1C(=O)CCC1=O)(=O)CCCCCCCCCCCCCCC([O-])=O.[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.C(O)(C(F)(F)F)=O>>[NH2:1][C@H:2]([C:12]([OH:14])=[O:13])[CH2:3][CH2:4][C:5](=[O:6])[OH:11]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 208637L-Glutamic acid di-tert-butyl esterHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 131727748Succinimidyl hexadecandioate

Product 1

HCID 33032L-Glutamic Acid

Procedure

This compound was prepared in analogy with example 4, via reaction of L-Glu(OtBu)-OtBu with succinimidyl hexadecandioate followed by activation with TSTU, coupling with Des(B30) human insulin and deprotection by TFA. LCMS 6130.8, calculated 6132.2.

Sources & evidence

ORD record
ord-d1837f8ca0c74a208a5d17b723bb0257
Source dataset
uspto-grants-2009_11
Patent number
US07615532B2

Linked notes

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