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10009-20-8

Basic Information
CAS No.: 10009-20-8
Name: N-6-Trifluoroacetyl-L-lysine
Molecular Structure:
Molecular Structure of 10009-20-8 (N-6-Trifluoroacetyl-L-lysine)
Formula: C8H13F3N2O3
Molecular Weight: 242.20
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;
EINECS: 1308068-626-2
Density: 1.333 g/cm3
Melting Point: 258 °C
Boiling Point: 382.5 °C at 760 mmHg
Flash Point: 185.1 °C
Solubility: 2 M HCl: 10 mg/mL, clear, colorless
Appearance:
Hazard Symbols:
Risk Codes:
Safety: 22-24/25
Transport Information:
PSA: 92.42000
LogP: 1.33830
Synthetic route
383-63-1

ethyl trifluoroacetate,

657-27-2, 10098-89-2

L-Lysine hydrochloride

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%
383-63-1

ethyl trifluoroacetate,

16079-52-0

sodium salt of L-lysine

A

10009-20-8

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

B

329-53-3

Nα,Nε-bis(trifluoroacetyl)-L-lysine

Conditions
ConditionsYield
In ethanol at 5 - 20℃;A 25%
B 56%
383-64-2

S-ethyl trifluoroacetate

657-27-2, 10098-89-2

L-Lysine hydrochloride

10009-20-8

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

Conditions
ConditionsYield
With sodium hydroxide
24424-99-5

di-tert-butyl dicarbonate

10009-20-8

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

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

86298-24-0

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

C15H18F3N3O4

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

phosgene

10009-20-8

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

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%
10009-20-8

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

530-62-1

1,1'-carbonyldiimidazole

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

Conditions
ConditionsYield
In tetrahydrofuran for 0.4h; Reflux; Large scale;81.9%
32315-10-9

bis(trichloromethyl) carbonate

10009-20-8

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

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℃;
10009-20-8

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

503-38-8

trichloromethyl chloroformate

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%
10009-20-8

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

121-44-8

triethylamine

14470-28-1

mono-4-methoxytrityl chloride

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%
590-28-3

potassium cyanate

10009-20-8

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

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;
10009-20-8

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

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

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

methanol

10009-20-8

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

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%
10009-20-8

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

366001-61-8

C16H22F6N4O4

Conditions
ConditionsYield
phosphorus pentoxide In 1-methyl-pyrrolidin-2-one at 170℃; Product distribution / selectivity;59%
10009-20-8

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

501-53-1

benzyl chloroformate

14905-30-7

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

Conditions
ConditionsYield
With sodium hydrogencarbonate
75-44-5

phosgene

10009-20-8

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

A

42267-27-6

Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride

B

112139-30-7

C9H11Cl2F3N2O3

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

phosgene

10009-20-8

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

112139-31-8

C9H12ClF3N2O4

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

chloro-trimethyl-silane

10009-20-8

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

110579-79-8

C11H21F3N2O3Si

Conditions
ConditionsYield
In chloroform; acetonitrile for 2h; Heating;
10009-20-8

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

10416-59-8, 132255-83-5

N,O-Bis(trimethylsilyl)acetamide

C14H29F3N2O3Si2

Conditions
ConditionsYield
In 1,4-dioxane
10009-20-8

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

7669-54-7

2-nitrobenzenesulfenyl chloride

41918-63-2

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

Conditions
ConditionsYield
With sodium hydroxide In acetone
10009-20-8

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

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

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
10009-20-8

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

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
10009-20-8

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

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
10009-20-8

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

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
10009-20-8

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

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
10009-20-8

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

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
10009-20-8

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

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
10009-20-8

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

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
10009-20-8

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

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
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  • N-6-Trifluoroacetyl-L-lysine   CAS: 10009-20-8

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    N-6-Trifluoroacetyl-L-lysine CAS: 10009-20-8

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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