Product Name

  • Name

    N-6-Trifluoroacetyl-L-lysine

  • EINECS 1308068-626-2
  • CAS No. 10009-20-8
  • Article Data4
  • CAS DataBase
  • Density 1.333 g/cm3
  • Solubility 2 M HCl: 10 mg/mL, clear, colorless
  • Melting Point 258 °C
  • Formula C8H13F3N2O3
  • Boiling Point 382.5 °C at 760 mmHg
  • Molecular Weight 242.198
  • Flash Point 185.1 °C
  • Transport Information
  • Appearance
  • Safety 22-24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 10009-20-8 (N-6-Trifluoroacetyl-L-lysine)
  • Hazard Symbols
  • Synonyms L-Lysine,N6-(trifluoroacetyl)- (9CI);Lysine, N6-(trifluoroacetyl)-, L- (8CI);(S)-6-(Trifluoroacetylamino)-2-aminohexanoic acid;N6-(Trifluoroacetyl)-L-lysine;N6-(Trifluoroacetyl)lysine;Ne-Trifluoroacetyl-L-lysine;Nw-(Trifluoroacetyl)-L-lysine;H-Lys(Tfa)-OH;
  • PSA 92.42000
  • LogP 1.33830

Synthetic route

ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

L-Lysine hydrochloride
657-27-2, 10098-89-2

L-Lysine hydrochloride

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Conditions
ConditionsYield
With sodium In ethanol at 5 - 20℃;62%
Stage #1: L-Lysine hydrochloride With ethanol; sodium
Stage #2: ethyl trifluoroacetate, In ethanol at 20℃; Cooling with ice;
Stage #3: With acetic acid In ethanol		62%
Stage #1: L-Lysine hydrochloride With sodium In ethanol for 1h;
Stage #2: ethyl trifluoroacetate, at 5 - 20℃; for 3h;
Stage #3: With acetic acid for 0.166667h;		56%
ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

sodium salt of L-lysine
16079-52-0

sodium salt of L-lysine

A

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

B

Nα,Nε-bis(trifluoroacetyl)-L-lysine
329-53-3

Nα,Nε-bis(trifluoroacetyl)-L-lysine

Conditions
ConditionsYield
In ethanol at 5 - 20℃;A 25%
B 56%
...Expand
S-ethyl trifluoroacetate
383-64-2

S-ethyl trifluoroacetate

L-Lysine hydrochloride
657-27-2, 10098-89-2

L-Lysine hydrochloride

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Conditions
ConditionsYield
With sodium hydroxide
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

(S)-6-trifluoroacetylamino-2-(tert-butoxycarbonylamino)-hexanoic acid
96561-04-5, 16965-06-3

(S)-6-trifluoroacetylamino-2-(tert-butoxycarbonylamino)-hexanoic acid

Conditions
ConditionsYield
Stage #1: di-tert-butyl dicarbonate; (S)-6-trifluoroacetylamino-2-aminohexanoic acid With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h;
Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide pH=2;		92%
In N,N-dimethyl-formamide at 20℃; for 2h;92%
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

N-phenyl-1H-benzo[d][1,2,3]triazole-1-carboxamide
86298-24-0

N-phenyl-1H-benzo[d][1,2,3]triazole-1-carboxamide

C15H18F3N3O4

C15H18F3N3O4

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃; for 0.5h; chemoselective reaction;92%
phosgene
75-44-5

phosgene

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride
42267-27-6

Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride

Conditions
ConditionsYield
In tetrahydrofuran at 20 - 30℃; for 4.33333h; Inert atmosphere;86.5%
In 1,4-dioxane at 45℃; for 2h;70%
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

N-(4-(2,5-dioxo-4-oxazolidinyl)butyl)-2,2,2-trifluoroacetamide

N-(4-(2,5-dioxo-4-oxazolidinyl)butyl)-2,2,2-trifluoroacetamide

Conditions
ConditionsYield
In tetrahydrofuran for 0.4h; Reflux; Large scale;81.9%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride
42267-27-6

Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran at 50℃; Inert atmosphere;75%
With Pinene In ethyl acetate at 105 - 110℃;
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride
42267-27-6

Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride

Conditions
ConditionsYield
In tetrahydrofuran for 2h; Inert atmosphere; Reflux;75%
With sodium hydroxide In tetrahydrofuran for 2h; Inert atmosphere; Reflux;75%
In ethyl acetate at 70℃; for 4h;63%
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

triethylamine
121-44-8

triethylamine

mono-4-methoxytrityl chloride
14470-28-1

mono-4-methoxytrityl chloride

C6H15N*C28H29F3N2O4

C6H15N*C28H29F3N2O4

Conditions
ConditionsYield
Stage #1: (S)-6-trifluoroacetylamino-2-aminohexanoic acid With chloro-trimethyl-silane; triethylamine In dichloromethane for 2h; Reflux; Inert atmosphere;
Stage #2: mono-4-methoxytrityl chloride In dichloromethane for 2h; Reflux; Inert atmosphere;
Stage #3: triethylamine In methanol; dichloromethane for 0.5h; Inert atmosphere;		74%
...Expand
potassium cyanate
590-28-3

potassium cyanate

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Nα-carbamoyl-Nε-trifluoroacetyl-L-lysine

Nα-carbamoyl-Nε-trifluoroacetyl-L-lysine

Conditions
ConditionsYield
In water at 50℃; for 3h; pH=7.5;73.8%
In water at 50℃; pH=8; Kinetics;
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

docosa-10,12-diynedioic acid mono-(2,5-dioxo-pyrrolidin-1-yl) ester
340701-06-6

docosa-10,12-diynedioic acid mono-(2,5-dioxo-pyrrolidin-1-yl) ester

21-[(S)-1-Carboxy-5-(2,2,2-trifluoro-acetylamino)-pentylcarbamoyl]-henicosa-10,12-diynoic acid

21-[(S)-1-Carboxy-5-(2,2,2-trifluoro-acetylamino)-pentylcarbamoyl]-henicosa-10,12-diynoic acid

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran at 20℃; for 24h; pH=9;62%
methanol
67-56-1

methanol

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

methyl 2-bromo-6-(2,2,2-trifluoroacetamido)hexanoate

methyl 2-bromo-6-(2,2,2-trifluoroacetamido)hexanoate

Conditions
ConditionsYield
Stage #1: (S)-6-trifluoroacetylamino-2-aminohexanoic acid With sulfuric acid; hydrogen bromide; sodium bromide; sodium nitrite In water at 3 - 20℃; Inert atmosphere;
Stage #2: methanol With toluene-4-sulfonic acid at 65℃; Inert atmosphere;		62%
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

C16H22F6N4O4
366001-61-8

C16H22F6N4O4

Conditions
ConditionsYield
phosphorus pentoxide In 1-methyl-pyrrolidin-2-one at 170℃; Product distribution / selectivity;59%
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

benzyl chloroformate
501-53-1

benzyl chloroformate

(2S)-2-{[(benzyloxy)carbonyl]amino}-6-[(trifluoroacetyl)amino]hexanoic acid
14905-30-7

(2S)-2-{[(benzyloxy)carbonyl]amino}-6-[(trifluoroacetyl)amino]hexanoic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate
phosgene
75-44-5

phosgene

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

A

Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride
42267-27-6

Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride

B

C9H11Cl2F3N2O3
112139-30-7

C9H11Cl2F3N2O3

Conditions
ConditionsYield
In tetrahydrofuran; N,N-dimethyl-formamide at 30℃; for 2.5h; Title compound not separated from byproducts;
...Expand
phosgene
75-44-5

phosgene

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

C9H12ClF3N2O4
112139-31-8

C9H12ClF3N2O4

Conditions
ConditionsYield
In tetrahydrofuran at 30℃; for 2.5h;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

C11H21F3N2O3Si
110579-79-8

C11H21F3N2O3Si

Conditions
ConditionsYield
In chloroform; acetonitrile for 2h; Heating;
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

N,O-Bis(trimethylsilyl)acetamide
10416-59-8, 132255-83-5

N,O-Bis(trimethylsilyl)acetamide

C14H29F3N2O3Si2

C14H29F3N2O3Si2

Conditions
ConditionsYield
In 1,4-dioxane
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

2-nitrobenzenesulfenyl chloride
7669-54-7

2-nitrobenzenesulfenyl chloride

Nα-(o-nitrophenylsulfenyl)-Nε-(trifluoroacetyl)lysine
41918-63-2

Nα-(o-nitrophenylsulfenyl)-Nε-(trifluoroacetyl)lysine

Conditions
ConditionsYield
With sodium hydroxide In acetone
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

21-((S)-5-Amino-1-carboxy-pentylcarbamoyl)-henicosa-10,12-diynoic acid
736142-36-2

21-((S)-5-Amino-1-carboxy-pentylcarbamoyl)-henicosa-10,12-diynoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 62 percent / aq. KOH / tetrahydrofuran / 24 h / 20 °C / pH 9
2: 46 percent / aq. KOH / tetrahydrofuran; methanol / 12 h / 35 °C / pH 12 - 13
View Scheme
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Boc-Ser-Lys(TFA)-Pro-Met-Gly(OBzl)2

Boc-Ser-Lys(TFA)-Pro-Met-Gly(OBzl)2

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: CHCl3; acetonitrile / 2 h / Heating
2: 48 percent / pyridine, triethylamine, pivaloyl chloride / CHCl3; acetonitrile / 1 h / Ambient temperature
3: 53 percent / diphenylphosphorazide, triethylamine / dioxane; dimethylformamide / 7 h, 0 deg C; 40 h, 20 deg C
View Scheme
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Nα-tert-butyloxycarbonyl-L-seryl-Nε-trifluoroacetyl-L-lysine
107994-57-0

Nα-tert-butyloxycarbonyl-L-seryl-Nε-trifluoroacetyl-L-lysine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CHCl3; acetonitrile / 2 h / Heating
2: 48 percent / pyridine, triethylamine, pivaloyl chloride / CHCl3; acetonitrile / 1 h / Ambient temperature
View Scheme
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Nα-(o-nitrophenylsulfenyl)-Nε-(trifluoroacetyl)-L-lysine N-hydroxysuccinimide ester
64851-79-2

Nα-(o-nitrophenylsulfenyl)-Nε-(trifluoroacetyl)-L-lysine N-hydroxysuccinimide ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2N NaOH / acetone
2: dicyclohexylcarbodiimide / dioxane; CH2Cl2 / 7 h / 0 - 20 °C
View Scheme
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

N-tert-butoxycarbonyl-L-leucyl-Nε-(trifluoroacetyl)-L-lysyl-L-leucine methyl ester
82175-93-7

N-tert-butoxycarbonyl-L-leucyl-Nε-(trifluoroacetyl)-L-lysyl-L-leucine methyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 2N NaOH / acetone
2: dicyclohexylcarbodiimide / dioxane; CH2Cl2 / 7 h / 0 - 20 °C
3: 1.) triethylamine / 1.) dioxane, methylene chloride, 15 min, 2.) 0 - 20 deg C, 7 h
4: HCl / ethyl acetate; diethyl ether / 0.33 h / 20 °C
5: 69.5 percent / triethylamine / dioxane; CH2Cl2 / 16 h / 0 - 20 °C
View Scheme
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Nα-(o-nitrophenylsulfenyl)-Nε-(trifluoroacetyl)-L-lysyl-L-leucine methyl ester
82175-92-6

Nα-(o-nitrophenylsulfenyl)-Nε-(trifluoroacetyl)-L-lysyl-L-leucine methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2N NaOH / acetone
2: dicyclohexylcarbodiimide / dioxane; CH2Cl2 / 7 h / 0 - 20 °C
3: 1.) triethylamine / 1.) dioxane, methylene chloride, 15 min, 2.) 0 - 20 deg C, 7 h
View Scheme
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Nε-(trifluoroacetyl)-L-lysyl-L-leucine methyl ester hydrochloride

Nε-(trifluoroacetyl)-L-lysyl-L-leucine methyl ester hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 2N NaOH / acetone
2: dicyclohexylcarbodiimide / dioxane; CH2Cl2 / 7 h / 0 - 20 °C
3: 1.) triethylamine / 1.) dioxane, methylene chloride, 15 min, 2.) 0 - 20 deg C, 7 h
4: HCl / ethyl acetate; diethyl ether / 0.33 h / 20 °C
View Scheme
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Nα-(o-nitrophenylsulfenyl)-Nε-(trifluoroacetyl)-L-lysyl-L-alanyl-L-alanine methyl ester
82175-94-8

Nα-(o-nitrophenylsulfenyl)-Nε-(trifluoroacetyl)-L-lysyl-L-alanyl-L-alanine methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2N NaOH / acetone
2: dicyclohexylcarbodiimide / dioxane; CH2Cl2 / 7 h / 0 - 20 °C
3: 50.9 percent / triethylamine / dioxane; CH2Cl2 / 16 h / 0 - 20 °C
View Scheme
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride
42267-27-6

Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran / 2.5 h / 30 °C
2: 88 percent / tetrahydrofuran / 4 h / 25 °C
View Scheme
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Nε-(trifluoroacetyl)-L-lysyl-L-proline
103300-89-6

Nε-(trifluoroacetyl)-L-lysyl-L-proline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran; dimethylformamide / 2.5 h / 30 °C
2: 94 percent Chromat. / tetrahydrofuran; H2O / 0.03 h / 0 - 12 °C
View Scheme
Multi-step reaction with 3 steps
1: tetrahydrofuran / 2.5 h / 30 °C
2: 88 percent / tetrahydrofuran / 4 h / 25 °C
3: 94 percent Chromat. / tetrahydrofuran; H2O / 0.03 h / 0 - 12 °C
View Scheme

N-6-Trifluoroacetyl-L-lysine Specification

The N-6-Trifluoroacetyl-L-lysine with CAS registry number of 10009-20-8 is also known as L-Lysine,N6-(trifluoroacetyl)- (9CI). The IUPAC name is (2S)-2-Amino-6-[(2,2,2-trifluoroacetyl)amino]hexanoic acid. It belongs to product categories of Chemical Intermediate for Lisinopril; API Intermediates. In addition, the formula is C8H13F3N2O3 and the molecular weight is 242.20. This chemical is soluble in hydrochloric acid and should be sealed in cool, dry place at the temperature of 2-8 °C. During using it, do not breathe dust and avoid contact with skin or eyes.

Physical properties about N-6-Trifluoroacetyl-L-lysine are: (1)ACD/LogP: -0.22; (2)ACD/LogD (pH 5.5): -2.72; (3)ACD/LogD (pH 7.4): -2.72; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 5; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 7; (11)Index of Refraction: 1.444; (12)Molar Refractivity: 48.25 cm3; (13)Molar Volume: 181.5 cm3; (14)Surface Tension: 39.5 dyne/cm; (15)Density: 1.333 g/cm3; (16)Flash Point: 185.1 °C; (17)Enthalpy of Vaporization: 69.27 kJ/mol; (18)Boiling Point: 382.5 °C at 760 mmHg; (19)Vapour Pressure: 6.55E-07 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
1. SMILES: FC(F)(F)C(=O)NCCCC[C@@H](C([O-])=O)[NH3+]
2. InChI: InChI=1/C8H13F3N2O3/c9-8(10,11)7(16)13-4-2-1-3-5(12)6(14)15/h5H,1-4,12H2,(H,13,16)(H,14,15)/t5-/m0/s1
3. InChIKey: PZZHRSVBHRVIMI-YFKPBYRVBT
4. Std. InChI: InChI=1S/C8H13F3N2O3/c9-8(10,11)7(16)13-4-2-1-3-5(12)6(14)15/h5H,1-4,12H2,(H,13,16)(H,14,15)/t5-/m0/s1
5. Std. InChIKey: PZZHRSVBHRVIMI-YFKPBYRVSA-N

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