(Z)-2-Acetylamino-4-methyl-pent-2-enoic acid
N-Ac-Leu
Conditions | Yield |
---|---|
With hydrogen; rhodium(I)-bis(1,5-cyclooctadiene) tetrafluoroborate; triethylamine; (2R,2'R)-bis(diphenylphosphino)-(1R,1'R)-dicyclopentane In tetrahydrofuran at 20℃; under 750.075 Torr; for 24h; | 100% |
With hydrogen; Rh(I)-(S)-chairphos In tetrahydrofuran Product distribution; Ambient temperature; other catalyst; other solvents; influence on products' optical yields; | |
With hydrogen; (S)-(-)-(6,6’-dimethoxybiphenyl-2,2’-diyl)bis(diphenylphosphine); [rhodium(I)(norborna-2,5-diene)2]SbF6 In dichloromethane at 20℃; under 1292.87 Torr; for 24h; | |
With chiral (1,1'-ferrocenediyl)bis(phospholo[3,4-d][1,3]dioxole); hydrogen; bis(1,5-cyclooctadiene)rhodium(I) hexafluorophosphate In tetrahydrofuran at 20℃; under 775.743 Torr; for 1h; |
Conditions | Yield |
---|---|
In water for 0.0666667h; Irradiation; | 98% |
With sodium hydrogencarbonate In water at 0 - 20℃; for 5h; | 89% |
With triethylamine In water at 20℃; | 35% |
methyl N-acetyl-leucinate
A
N-Ac-Leu
B
methyl (R)-2-(N-acetylamino)-4-methylpentanoate
Conditions | Yield |
---|---|
With sodium hydroxide; phosphate buffer; pronase EC 3.4.24.4 In tetrahydrofuran Ambient temperature; | A 79% B 91% |
Conditions | Yield |
---|---|
at 0 - 20℃; | 89% |
(S)-benzyl 2-acetamido-4-methylpentanoate
N-Ac-Leu
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In ethanol at 50℃; for 3h; | 81% |
With palladium 10% on activated carbon; hydrogen In ethanol at 50℃; for 3h; | 81% |
Conditions | Yield |
---|---|
With sodium hydroxide |
Conditions | Yield |
---|---|
With (-)-α-fenchylamine |
methyl N-acetyl-leucinate
N-Ac-Leu
Conditions | Yield |
---|---|
for 118h; carbonate hydrolyase EC 4.2.2.1 (bovine carbonic anhydrase, BCA), pH 7.5; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
In ethanol; water at 35℃; for 48h; Yield given; |
2-acetylamino-4-methyl-pent-2-enoic acid
N-Ac-Leu
Conditions | Yield |
---|---|
With hydrogen; <(2R,3R)-2,3-Bis(diphenylphosphino)butan>(ϖ-norbornadien)rhodium(I)-perchlorate In tetrahydrofuran under 3000.2 Torr; for 8h; Yield given; |
2-acetylamino-4-methyl-pent-2-enoic acid
A
N-Ac-Leu
B
N-acetyl-D-leucine
Conditions | Yield |
---|---|
With hydrogen; ClO4; (2R,3S)-1,2-bis(diphenylphosphino)-3-tBoc-aminobutane In ethanol for 22h; Ambient temperature; Yield given; | |
With ; hydrogen In ethanol at 20℃; under 760 Torr; Title compound not separated from byproducts; |
(Z)-2-Acetylamino-4-methyl-pent-2-enoic acid
A
N-Ac-Leu
B
N-acetyl-D-leucine
Conditions | Yield |
---|---|
With <(1R;2R-MAC-PONP)Rh(COD)>(+)BF4(-); hydrogen In methanol at 30℃; under 750.06 Torr; Title compound not separated from byproducts; | |
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; triethylamine; (2R,2'R)-bis(diphenylphosphino)-(1R,1'R)-dicyclopentane In tetrahydrofuran under 760 Torr; for 24h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With hydrogen; triethylamine; ClO4; (2S,4S)-MOD-BPPM In ethanol at 50℃; under 15200 Torr; for 20h; Title compound not separated from byproducts; |
(1'S,3S)-8-acetoxy-3-<1'-(acetylamino)-3'-methylbutyl>-3,4-dihydro-1-oxo-1H-2-benzopyran
N-Ac-Leu
Conditions | Yield |
---|---|
With potassium permanganate; magnesium sulfate In water for 1.5h; Heating; |
Conditions | Yield |
---|---|
β‐cyclodextrin In water; dimethyl sulfoxide at 25℃; Rate constant; Mechanism; various conditions; |
Conditions | Yield |
---|---|
With rice bran lipase; sodium chloride at 30℃; pH=7.5; Title compound not separated from byproducts; |
acetamide
carbon monoxide
isovaleraldehyde
A
N-Ac-Leu
B
N-acetyl-D-leucine
Conditions | Yield |
---|---|
With sulfuric acid; lithium bromide; bis(triphenylphosphine)palladium dibromide In various solvent(s) at 120℃; under 45003.6 Torr; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
DL-leucine methyl ester
N-Ac-Leu
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: NaOCH3 / Brenner esterification 2: pyridine 3: H2O; ethanol / 48 h / 35 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine 2: H2O; ethanol / 48 h / 35 °C View Scheme |
(3S)-3-<(1'S)-1'-amino-3'-methylbutyl>-3,4-dihydro-8-hydroxy-1H-2-benzopyran-1-one
N-Ac-Leu
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 91 percent / pyridine / 2 h / 50 °C 2: KMnO4, MgSO4 / H2O / 1.5 h / Heating View Scheme |
C8H13NO3
N-Ac-Leu
Conditions | Yield |
---|---|
With {Rh[ZhangPhos](nbd)}BF4; hydrogen In methanol at 20℃; under 1034.32 Torr; for 12h; optical yield given as %ee; enantioselective reaction; |
Conditions | Yield |
---|---|
With potassium carbonate In 1,4-dioxane; water |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / ethanol / 3 h / 50 °C View Scheme | |
Multi-step reaction with 2 steps 1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / ethanol / 3 h / 50 °C View Scheme |
(S)-2-[1 (3-ethoxy-4-methoxyphenyl)]-1-methanesulfonyl-2-ethylamine
N-Ac-Leu
(S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine-(S)-2-acetamido-4-methylpentanoate
Conditions | Yield |
---|---|
In methanol for 1h; Reflux; | 98.3% |
In methanol at 65 - 70℃; | |
In methanol for 1h; Reflux; | 1670 g |
2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine
N-Ac-Leu
Conditions | Yield |
---|---|
In methanol at 20℃; for 4h; Reflux; | 98% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 4.5h; | 98% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 8h; | 96% |
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 0 - 20℃; for 4.5h; | 96% |
N-Ac-Leu
(4R,5S)-1,5-Dimethyl-3-((2R,3S)-3-methyl-aziridine-2-carbonyl)-4-phenyl-imidazolidin-2-one
N-{(S)-1-[(2R,3S)-2-((4S,5R)-3,4-Dimethyl-2-oxo-5-phenyl-imidazolidine-1-carbonyl)-3-methyl-aziridine-1-carbonyl]-3-methyl-butyl}-acetamide
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In dichloromethane; acetonitrile for 12h; Ambient temperature; | 95% |
N-Ac-Leu
benzyl (R)-aziridine-2-carboxylate
benzyl (2R,2'S)-1-(2'-acetamido-4'-methylpentanoyl)aziridine-2-carboxylate
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane; N,N-dimethyl-formamide at 0℃; for 6h; Acylation; | 95% |
N-Ac-Leu
(4R,5S,2'R)-1,5-dimethyl-3-[(2'-aziridinyl)carbonyl]-4-phenylimidazolidin-2-one
(4R,5S,2'R,2''S)-1,5-dimethyl-3-{[1'-(2''-acetamido-4''-methylpentanoyl)-2'-aziridinyl]carbonyl}-4-phenylimidazolidin-2-one
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane; N,N-dimethyl-formamide at 0℃; for 6h; Acylation; | 95% |
Conditions | Yield |
---|---|
Stage #1: N-Ac-Leu With caesium carbonate In acetonitrile at 20℃; for 0.333333h; Stage #2: 2,2,2-trifluoroethyl trifluoromethanesulphonate In acetonitrile at 20℃; for 3h; | 94% |
Conditions | Yield |
---|---|
With K10 clay for 0.0333333h; Cyclization; microwave irradiation; | 93% |
With diethyldichlorosilane Heating; | 60% |
With toluene-4-sulfonic acid In benzene Heating; | |
With toluene-4-sulfonic acid In toluene |
[(S)-1-((S)-1-{(S)-[(2R,3S)-2-((S)-1-Butylcarbamoyl-2-methyl-propylcarbamoyl)-tetrahydro-furan-3-yl]-hydroxy-methyl}-3-methyl-butylcarbamoyl)-3-methylsulfanyl-propyl]-carbamic acid tert-butyl ester
N-Ac-Leu
Conditions | Yield |
---|---|
With hydrogenchloride In various solvents at 0 - 5℃; | 92% |
Conditions | Yield |
---|---|
Solid phase reaction; | 90% |
2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine
N-Ac-Leu
(S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine-(S)-2-acetamido-4-methylpentanoate
Conditions | Yield |
---|---|
In methanol at 20℃; for 8h; Reflux; Resolution of racemate; | 90% |
Stage #1: 2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine; N-Ac-Leu In methanol for 1h; Reflux; Stage #2: In methanol at 20℃; for 4h; Reflux; | 90% |
In methanol at 20℃; for 4h; Reflux; | 90% |
Conditions | Yield |
---|---|
In ethanol; benzene byproducts: H2O; acid:R2SnO molar ratio 1:1, benzene-ethanol; azeotropic removal of water, filtered, solvent was removed; solidified on trituration with petroleum ether; elem. anal.; | 90% |
Conditions | Yield |
---|---|
In ethanol; benzene byproducts: H2O; acid:R2SnO molar ratio 1:1, benzene-ethanol; azeotropic removal of water, filtered, solvent was removed; solidified on trituration with petroleum ether; elem. anal.; | 90% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide | 89% |
Stage #1: N-Ac-Leu With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 24h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 25℃; for 24h; |
N-Ac-Leu
N-methylglycine methyl ester hydrochloride
Conditions | Yield |
---|---|
Stage #1: N-Ac-Leu With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.166667h; Stage #2: N-methylglycine methyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; | 89% |
Conditions | Yield |
---|---|
With thionyl chloride at 0℃; for 4h; | 88% |
Conditions | Yield |
---|---|
In ethanol; benzene byproducts: H2O; acid:R2SnO molar ratio 1:1, benzene-ethanol; azeotropic removal of water, filtered, solvent was removed; solidified on trituration with petroleum ether; elem. anal.; | 87% |
N-Ac-Leu
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; HATU In acetonitrile at 20℃; for 2h; Inert atmosphere; | 87% |
Conditions | Yield |
---|---|
Stage #1: C12H14(2)H3NO4S With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; (R)-(-)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; deuterium In 2,2,2-trifluoroethanol at 50℃; under 2585.81 Torr; for 16h; Stage #2: N-Ac-Leu In methanol at 20 - 55℃; | 86% |
N-Ac-Leu
Conditions | Yield |
---|---|
With potassium carbonate; sodium iodide In acetone at 70℃; for 1h; | 86% |
1-hydroxy-pyrrolidine-2,5-dione
N-Ac-Leu
N-acetyl-L-leucine N-hydroxysuccinimide ester
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; | 85% |
Conditions | Yield |
---|---|
Stage #1: C12H14(2)H3NO4S With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; (R)-(-)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; deuterium In methanol; 2,2,2-trifluoroethanol at 50℃; under 2585.81 Torr; for 16h; Stage #2: N-Ac-Leu In methanol at 20 - 55℃; | 85% |
Conditions | Yield |
---|---|
Stage #1: C12H10(2)H7NO4S With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; (R)-(-)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; deuterium In 2,2,2-trifluoroethanol at 50℃; under 2585.81 Torr; for 16h; Stage #2: N-Ac-Leu In methanol at 20 - 55℃; for 1h; | 85% |
Conditions | Yield |
---|---|
Stage #1: C12H5(2)H12NO4S With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; (R)-(-)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; deuterium In 2,2,2-trifluoroethanol at 50℃; under 2585.81 Torr; for 16h; Stage #2: N-Ac-Leu In methanol at 55℃; for 1h; | 85% |
1. Introduction of N-Acetyl-L-leucine
N-Acetyl-L-leucine, with the IUPAC Name: (2S)-2-acetamido-4-methylpentanoic acid, is one kind of powder.
And it belongs to the Product Categories which include Amino Acids Derivatives; Amino Acid Derivatives; Amino Acids; Leucine [Leu, L]; Amino Acids and Derivatives; Ac-Amino Acids; Amino Acids (N-Protected); Biochemistry; N-Acetyl-Amino acid series; Amino Acid Derivatives; Leucine; Peptide Synthesis. When comes to the application, it is one type of biochemical reagent.
2. Properties of N-Acetyl-L-leucine
N-Acetyl-L-leucine has the following property datas: (1)XLogP3: 0.5; (2)H-Bond Donor: 2; (3)H-Bond Acceptor: 3; (4)EINECS: 214-706-3; (5)Melting Point: 187-190 °C(lit.); (6)Surface Tension: 37.2 dyne/cm; (7)Water Solubility: 0.81 g/100 mL (20 °C); (8)Density: 1.069 g/cm3; (9)Flash Point: 177.4 °C; (10)Enthalpy of Vaporization: 67.7 kJ/mol; (11)Boiling Point: 369.7 °C at 760 mmHg; (12)Vapour Pressure: 1.77E-06 mmHg at 25°C. When comes to the usage, it could be used for treating vestibular-related imbalance and vertigo.
3. Safty information about N-Acetyl-L-leucine
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36-26
S24/25:Avoid contact with skin and eyes.
S36:Wear suitable protective clothing.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
HazardClass: IRRITANT
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