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16965-06-3

16965-06-3 Structure

16965-06-3 Structure
IdentificationBack Directory
[Name]

BOC-LYS(TFA)-OH
[CAS]

16965-06-3
[Synonyms]

NSC 164662
16965-06-3
BOC-LYS(TFA)-OH
BOC-L-LYS(TFA)-OH
BOC-LYSINE(TFA)-OH
BOC-N-E-TFA-L-LYSINE
BOC-LYS(TFA)-OH USP/EP/BP
BOC-N-EPSILON-TFA-L-LYSINE
N-ALPHA-T-BOC-NE-TFA-L-LYS
Boc-(Trifluoroacetyl) Lysine
(Tert-Butoxy)Carbonyl Lys(Tfa)-OH
Nα-Boc-Nε-trifluoroacetyl-L-lysine
N-α-Boc-N-ε-trifluoroacetyl-L-lysine
BOC-N-EPSILON-TRIFLUOROACETYL-L-LYSINE
N^a-Boc-N^e-trifluoroacetyl-L-lysine,95%
N^a-Boc-N^e-trifluoroacetyl-L-lysine, 95%
N2-Boc-N6-(2,2,2-trifluoroacetyl)-L-lysine
Nα-Boc-Nε-trifluoroacetyl-L-lysine≥ 99% (HPLC)
N-ALPHA-BOC-N-EPSILON-TRIFLUOROACETYL-L-LYSINE
N-ALPHA-T-BOC-N-EPSILON-TRIFLUOROACETYL-L-LYSINE
N2-tert-Butoxycarbonyl-N6-trifluoroacetyl-L-lysine
N-ALPHA-T-BUTOXYCARBONYL-N-EPSILON-TRIFLUOROACETYL-L-LYSINE
N-ALPHA-T-BUTYLOXYCARBONYL-N-EPSILON-TRIFLUORACETYL-L-LYSINE
NALPHA-tert-Butoxycarbonyl-NEPSILON-trifluoroacetyl-L -lysine
N-ALPHA-TERT-BUTYLOXYCARBONYL-N-EPSILON-TRIFLUORACETYL-L-LYSINE
N2-[(1,1-Dimethylethoxy)carbonyl]-N6-(2,2,2-trifluoroacetyl)-L-lysine
(S)-6-(Trifluoroacetylamino)-2-(tert-butoxycarbonylamino)hexanoic acid
L-Lysine, N2-[(1,1-dimethylethoxy)carbonyl]-N6-(2,2,2-trifluoroacetyl)-
(2S)-2-{[(tert-butoxy)carbonyl]amino}-6-(trifluoroacetamido)hexanoic acid
(S)-2-((tert-Butoxycarbonyl)amino)-6-(2,2,2-trifluoroacetamido)hexanoicaci
(S)-2-((tert-Butoxycarbonyl)aMino)-6-(2,2,2-trifluoroacetaMido)hexanoic acid
(2S)-2-{[(tert-butoxy)carbonyl]amino}-6-(2,2,2-trifluoroacetamido)hexanoic acid
2-[[(2-methylpropan-2-yl)oxy-oxomethyl]amino]-6-[(2,2,2-trifluoro-1-oxoethyl)amino]hexanoic acid
[Molecular Formula]

C13H21F3N2O5
[MDL Number]

MFCD00037104
[MOL File]

16965-06-3.mol
[Molecular Weight]

342.31
Chemical PropertiesBack Directory
[Melting point ]

102-105 °C
[Boiling point ]

485.6±45.0 °C(Predicted)
[density ]

1.254±0.06 g/cm3(Predicted)
[storage temp. ]

-15°C
[solubility ]

Soluble in DMSO.
[form ]

Powder
[pka]

3.97±0.21(Predicted)
[color ]

White
[Optical Rotation]

-12.72°(C=0.87g/100mI, DMF, 20°C, 589nm)
Safety DataBack Directory
[WGK Germany ]

3
[F ]

10-21
[HazardClass ]

IRRITANT
Hazard InformationBack Directory
[Chemical Properties]

White powder
[Uses]

Boc-Lys(Tfa)-OH (cas# 16965-06-3) is a compound useful in organic synthesis.
[Synthesis]

Di-tert-butyl dicarbonate

24424-99-5

N-6-Trifluoroacetyl-L-lysine

10009-20-8

BOC-D-LYS(TFA)-OH

96561-04-5

The general procedure for the synthesis of N2-(tert-butoxycarbonyl)-N6-(2,2,2-trifluoroacetyl)-D-lysine from di-tert-butyl dicarbonate and trifluoroacetyl-lysine was as follows: trifluoroacetyl-lysine (3.63 g, 0.015 mol) was suspended in 40 ml of N,N-dimethylformamide (DMF), to which was added triethylamine (TEA, 3.03 g , 0.03 mol) and di-tert-butyl dicarbonate (3.6 g, 0.0165 mol). The reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, the mixture was diluted with water to three times the original volume and acidified with hydrochloric acid to pH 2. The product was extracted with ethyl acetate (EtOAc, 100 ml), the organic phase was washed with water and saturated brine sequentially and dried with anhydrous magnesium sulfate (MgSO4). The solvent was removed by distillation under reduced pressure to afford (S)-2-((tert-butoxycarbonyl)amino)-6-(2,2,2-trifluoroacetamido)hexanoic acid (4.7 g, 92% yield). The analytical data of the product (3) were in agreement with literature reports.

[References]

[1] Patent: WO2009/114809, 2009, A1. Location in patent: Page/Page column 7-8
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 1, p. 255 - 258
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