Conditions | Yield |
---|---|
Stage #1: methanol With thionyl chloride for 1h; Cooling with ice; Stage #2: L-leucine at 20 - 66℃; for 6.5h; | 100% |
With thionyl chloride at 20℃; for 4h; | 99% |
With thionyl chloride | 99% |
Alloc-Leu-OMe
methyl (L)-leucinate hydrochloride
Conditions | Yield |
---|---|
With triethylsilane; chloroform; palladium on activated charcoal In methanol for 0.0833333h; | 100% |
(S)-2-(2-Aza-bicyclo[2.2.1]hept-5-en-2-yl)-4-methyl-pentanoic acid methyl ester
methyl (L)-leucinate hydrochloride
Conditions | Yield |
---|---|
Bio-Rad AG 50W-X2 In ethanol at 73℃; for 1h; | 98% |
Conditions | Yield |
---|---|
With thionyl chloride In methanol | 98% |
94% | |
Multi-step reaction with 2 steps 1: thionyl chloride View Scheme |
Conditions | Yield |
---|---|
In methanol at 20℃; for 24h; | 98% |
Conditions | Yield |
---|---|
With thionyl chloride at 0℃; | 94% |
With acetyl chloride at 20℃; for 0.5h; |
methyl (S)-2-methoxycarbonylamino-4-methyl-valerate
methyl (L)-leucinate hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride at 20℃; |
Conditions | Yield |
---|---|
With hydrogenchloride In water |
N-benzyloxycarbonyl-L-leucine methyl ester
methyl (L)-leucinate hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; acetic acid In water |
methanol
N-tert-butoxycarbonyl-L-leucine
methyl (L)-leucinate hydrochloride
Conditions | Yield |
---|---|
With thionyl chloride Inert atmosphere; Reflux; | |
With thionyl chloride at 20℃; Cooling; | |
With thionyl chloride at 50℃; for 5h; Inert atmosphere; |
methyl (L)-leucinate hydrochloride
4-methoxy-benzaldehyde
(S)-2-{[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-amino}-4-methyl-pentanoic acid methyl ester
Conditions | Yield |
---|---|
With sodium carbonate In methanol for 12h; Ambient temperature; | 100% |
With 4 A molecular sieve; titanium tetrachloride; sodium sulfate; triethylamine In dichloromethane at 20℃; for 8h; | 92% |
methyl (L)-leucinate hydrochloride
orthoformic acid triethyl ester
(S)-methyl 2-formamido-4-methylpentanoate
Conditions | Yield |
---|---|
at 95℃; for 1h; | 100% |
methyl (L)-leucinate hydrochloride
benzyl chloroformate
N-benzyloxycarbonyl-L-leucine methyl ester
Conditions | Yield |
---|---|
With sodium carbonate In 1,4-dioxane for 4h; Ambient temperature; | 100% |
With triethylamine In dichloromethane at 20℃; | 80% |
With sodium hydrogencarbonate In diethyl ether; water at 0 - 20℃; for 3h; | 63% |
Stage #1: methyl (L)-leucinate hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.25h; Inert atmosphere; Stage #2: benzyl chloroformate In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; | |
With sodium carbonate In water at 20℃; for 16h; |
methyl (L)-leucinate hydrochloride
phenyl chloroformate
N-benzyloxycarbonyl-L-leucine methyl ester
Conditions | Yield |
---|---|
With sodium carbonate In 1,4-dioxane; water | 100% |
methyl (L)-leucinate hydrochloride
sodium carbonate
phenyl chloroformate
N-benzyloxycarbonyl-L-leucine methyl ester
Conditions | Yield |
---|---|
In 1,4-dioxane; water | 100% |
C10H12O4
methyl (L)-leucinate hydrochloride
N-[(2S,3R)-2,3-dihydroxy-4-phenylbutanoyl]-L-leucine methyl ester
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 1.5h; | 100% |
methyl (L)-leucinate hydrochloride
Nα,Nβ-bis(t-butoxycarbonyl)-L-α,β-diaminopropionic acid
N,N'-di-Boc-2,3-L-Dap-L-Leu-OMe
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; | 100% |
methyl (L)-leucinate hydrochloride
4-Phenylbutyric acid
(S)-methyl 4-methyl-2-(4-phenylbutanamido)pentanoate
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran at 20℃; for 5h; Cooling with ice; | 100% |
bromobenzene
methyl (L)-leucinate hydrochloride
A
biphenyl
B
(S)-2-amino-1,1-diphenyl-4-methylpentan-1-ol
Conditions | Yield |
---|---|
Stage #1: bromobenzene With magnesium In diethyl ether at 40℃; Inert atmosphere; Stage #2: methyl (L)-leucinate hydrochloride In diethyl ether at 0 - 20℃; for 15.5h; | A n/a B 100% |
(S)-2-(((benzyloxy)carbonyl)amino)-3-(4-(((tert-butoxycarbonyl)amino)methyl)phenyl)propanoic acid
methyl (L)-leucinate hydrochloride
Cbz-Phe(4-CH2NHBoc)-Leu-OMe
Conditions | Yield |
---|---|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane for 2h; | 100% |
Conditions | Yield |
---|---|
Stage #1: methyl (L)-leucinate hydrochloride; pyromellitic acid monoanhydride With N,N-dimethyl acetamide; triethylamine at 20℃; for 22h; Inert atmosphere; Stage #2: With acetic anhydride at 80℃; for 7h; Inert atmosphere; | 100% |
methyl (L)-leucinate hydrochloride
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20 - 50℃; for 14h; | 100% |
Conditions | Yield |
---|---|
Stage #1: C23H41N3O6 With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.5h; Stage #2: methyl (L)-leucinate hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; | 100% |
(S)-N-(tert-butoxycarbonyl)serine
methyl (L)-leucinate hydrochloride
(S)-2-((S)-2-tert-butoxycarbonylamino-3-hydroxypropanoylamino)-4-methylpentanoic acid methyl ester
Conditions | Yield |
---|---|
With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; pH=8 - 9; | 99% |
Stage #1: methyl (L)-leucinate hydrochloride With sodium carbonate In dichloromethane; water at 20℃; for 0.0833333h; Stage #2: (S)-N-(tert-butoxycarbonyl)serine With C12H6B2Br4O3 In 1,2-dichloro-ethane at 90℃; for 18h; chemoselective reaction; | 99% |
With 4-methyl-morpholine; dicyclohexyl-carbodiimide In acetonitrile 0 deg C, 2 h; room temp., overnight; | 70% |
methyl (L)-leucinate hydrochloride
benzoyl chloride
N-benzoyl-L-leucine methyl ester
Conditions | Yield |
---|---|
With potassium carbonate In chloroform for 3h; Heating; | 99% |
With N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate at 20℃; | 61% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; | 61% |
methyl (L)-leucinate hydrochloride
benzaldehyde
methyl (S)-2-(benzylideneamino)-4-methylpentanoate
Conditions | Yield |
---|---|
With triethylamine In chloroform at 0 - 20℃; for 24h; Inert atmosphere; Sealed tube; | 99% |
Stage #1: methyl (L)-leucinate hydrochloride With magnesium sulfate; triethylamine In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Stage #2: benzaldehyde In dichloromethane at 20℃; Inert atmosphere; | 98% |
With triethylamine In dichloromethane for 24h; Ambient temperature; |
BOC-glycine
methyl (L)-leucinate hydrochloride
(S)-methyl 2-(2-((tert-butoxycarbonyl)amino)acetamido)-4-methylpentanoate
Conditions | Yield |
---|---|
Stage #1: BOC-glycine With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1h; Inert atmosphere; Stage #2: methyl (L)-leucinate hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere; | 99% |
Stage #1: BOC-glycine With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl (L)-leucinate hydrochloride In dichloromethane at 20℃; for 1h; Inert atmosphere; | 98% |
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h; Inert atmosphere; | 97% |
methyl (L)-leucinate hydrochloride
4-Nitrobenzenesulfonyl chloride
(S)-methyl 4-methyl-2-(4-nitrophenylsulfonamido)pentanoate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 12h; Inert atmosphere; | 99% |
With triethylamine In dichloromethane at 20℃; for 0.5h; | 75% |
With pyridine In dichloromethane at 20℃; | |
Stage #1: methyl (L)-leucinate hydrochloride; 4-Nitrobenzenesulfonyl chloride In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at 20℃; for 11h; Inert atmosphere; | |
Stage #1: methyl (L)-leucinate hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 0.166667h; Stage #2: 4-Nitrobenzenesulfonyl chloride In dichloromethane at 0℃; |
acetoxolone
methyl (L)-leucinate hydrochloride
Conditions | Yield |
---|---|
Stage #1: acetoxolone With oxalyl dichloride In dichloromethane at 20℃; for 2h; Stage #2: methyl (L)-leucinate hydrochloride With triethylamine In dichloromethane at 20℃; | 99% |
methyl (L)-leucinate hydrochloride
N-tert-butoxycarbonyl-3-(2-naphthyl)-L-alanine
N-tert-butoxycarbonyl-L-tryptophan-L-leucine methylester
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; | 99% |
Conditions | Yield |
---|---|
With 4-methyl-morpholine; DMT*brucine tetrafluoroborate; brucine In acetonitrile at 0 - 20℃; optical yield given as %ee; enantioselective reaction; | 99% |
(S)-N-(benzyloxycarbonyl)valine
methyl (L)-leucinate hydrochloride
(S)-methyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanamido)-4-methylpentanoate
Conditions | Yield |
---|---|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 12h; | 99% |
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 12h; | 69% |
With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 0 - 20℃; | 69% |
bis(trichloromethyl) carbonate
methyl (L)-leucinate hydrochloride
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine In dichloromethane; water at 0 - 20℃; for 3h; | 99% |
bis(trichloromethyl) carbonate
methyl (L)-leucinate hydrochloride
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine In dichloromethane; water at 0 - 20℃; for 3h; | 99% |
bis(trichloromethyl) carbonate
methyl (L)-leucinate hydrochloride
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine In dichloromethane; water at 0 - 20℃; for 3h; | 99% |
bis(trichloromethyl) carbonate
methyl (L)-leucinate hydrochloride
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine In dichloromethane; water at 0 - 20℃; for 3h; | 99% |
4-(3-pyridylcarbamoyl)piperidine
bis(trichloromethyl) carbonate
methyl (L)-leucinate hydrochloride
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine In dichloromethane; water at 0 - 20℃; for 3h; | 99% |
C13H15ClN2O3
methyl (L)-leucinate hydrochloride
Conditions | Yield |
---|---|
Stage #1: C13H15ClN2O3 With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h; Stage #2: methyl (L)-leucinate hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3h; | 99% |
Product Name: L-leucine methyl ester (CAS NO.7517-19-3)
Molecular Formula: C7H16ClNO2
Molecular Weight: 181.660440 g/mol
Melting Point: 151-153 °C(lit.)
Solubility: H2O: 50 mg/mL, clear, colorless
Alpha: 20 °(c=4.5, MeOH)
Refractive index:13 °(C=2, H2O)
Storage temp.: 0-6°C
Sensitive: Hygroscopic
BRN: 3595133
Flash Point: 42.7 °C
Enthalpy of Vaporization: 40.56 kJ/mol
Boiling Point: 169.2 °C at 760 mmHg
Vapour Pressure: 1.56 mmHg at 25°C
H-Bond Donor: 2
H-Bond Acceptor: 3
Structure Descriptors of L-leucine methyl ester (CAS NO.7517-19-3):
IUPAC Name: methyl 2-amino-4-methylpentanoate hydrochloride
Canonical SMILES: CC(C)CC(C(=O)OC)N.Cl
InChI: InChI=1S/C7H15NO2.ClH/c1-5(2)4-6(8)7(9)10-3;/h5-6H,4,8H2,1-3H3;1H
InChIKey: DODCBMODXGJOKD-UHFFFAOYSA-N
Categories: Protected Amino Acids; Amino Acids; Leucine [Leu, L]; Amino Acids and Derivatives; Amino Acid Methyl Esters; Amino Acids (C-Protected); Biochemistry; Amino hydrochloride; Amino Acid Derivatives; Leucine; Peptide Synthesis
L-leucine methyl ester (CAS NO.7517-19-3) is a kind of biochemical reagents, pharmaceutical intermediates.
Safety Information of L-leucine methyl ester (CAS NO.7517-19-3):
Hazard Codes:Xi
Risk Statements:36/37/38
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:22-24/25-36/37/39-27-26
22:Do not breathe dust
24/25:Avoid contact with skin and eyes
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
27:Take off immediately all contaminated clothing
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany:3
L-leucine methyl ester , its CAS NO. is 7517-19-3, the synonyms are Methyl L-leucinate HCl ; Methyl L-leucinate hydrochloride .
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