methanol
L-methionine
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
Conditions | Yield |
---|---|
With acetyl chloride Reflux; | 100% |
With thionyl chloride at 0 - 45℃; for 10h; Inert atmosphere; | 99% |
With thionyl chloride at 0℃; for 16h; Inert atmosphere; Reflux; | 98% |
L-methionine
2,2-dimethoxy-propane
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In water at 20℃; | 96% |
With hydrogenchloride In water at 20℃; for 12h; | 82% |
With hydrogenchloride at 20℃; |
N-Pent-4-enoyl-L-methionine methyl ester
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride; iodine In tetrahydrofuran; water | 89% |
(S)-N-(tert-butoxycarbonyl)serine
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
tert-butoxycarbonylserylmethionine methyl ester
Conditions | Yield |
---|---|
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine In ethanol; dichloromethane at 20℃; for 48h; | 100% |
Stage #1: (S)-methyl 2-amino-4-(methylthio)butanoate 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 8h; chemoselective reaction; | 81% |
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
benzyl chloroformate
methyl (S)-2-(benzyloxycarbonylamino)-4-methylmercaptobutanoate
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In water; ethyl acetate at 0 - 5℃; for 4h; | 100% |
With sodium hydrogencarbonate In diethyl ether; water at 0 - 20℃; | 99% |
Stage #1: (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride With potassium carbonate In water at 0℃; Stage #2: benzyl chloroformate In water for 6h; | 99% |
With potassium hydrogencarbonate In water; ethyl acetate at 0℃; for 4h; | 90% |
With potassium hydrogencarbonate In water; ethyl acetate at 20℃; for 12h; Cooling with ice; | 86% |
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
(2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienoic acid
methyl (2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienyl methionine
Conditions | Yield |
---|---|
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 16h; Ambient temperature; | 100% |
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
phenyl isoselenocyanate
Conditions | Yield |
---|---|
Stage #1: (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride With triethylamine In tetrahydrofuran at 20℃; for 1h; Stage #2: phenyl isoselenocyanate In tetrahydrofuran for 4h; Heating; Further stages.; | 100% |
carbon monoxide
17-iodo-5α-androst-16-ene
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
C26H41NO3S
Conditions | Yield |
---|---|
With palladium diacetate; triethylamine; triphenylphosphine at 100℃; for 8h; | 100% |
2-(5,6-dimethoxy-1,3-dioxoisoindolin-2-yl)acetic acid
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
Conditions | Yield |
---|---|
Stage #1: 2-(5,6-dimethoxy-1,3-dioxoisoindolin-2-yl)acetic acid With triethylamine; isobutyl chloroformate In tetrahydrofuran at -25℃; for 0.5h; Stage #2: (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride In tetrahydrofuran; chloroform at -25℃; for 1.5h; | 100% |
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
methylamine
(S)-2-amino-N-methyl-4-(methylthio)butanamide
Conditions | Yield |
---|---|
In ethanol at 20℃; for 48h; | 100% |
N-tert-butoxycarbonyl-L-phenylalanine
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
Methyl ester of N-t-butyloxycarbonyl-L-phenylalanyl-L-methionine
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine; 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate In water at 20℃; for 1h; Green chemistry; | 99% |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 20℃; for 4h; Inert atmosphere; | 93% |
With pentafluorophenyl diphenyl-phosphinate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1.5h; Ambient temperature; | 81% |
N-phenyl-N-methylcarbamoyl chloride
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
methyl (S)-2-{[methyl(phenyl)carbamoyl]amino}-4-(methylsulfanyl)butanoate
Conditions | Yield |
---|---|
With triethylamine In acetonitrile for 21h; Reflux; | 99% |
With dmap; triethylamine In 1,2-dimethoxyethane for 2h; Inert atmosphere; Reflux; | 98% |
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
isononanoyl chloride
methyl (2S)-4-(methylthio)-2-(3,5,5-trimethylhexanamido)butanoate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 99% |
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
benzaldehyde
methyl-2-(benzylideneamino)-4-(methylthio)butyrate
Conditions | Yield |
---|---|
With sodium carbonate; magnesium sulfate; triethylamine In dichloromethane at 20℃; for 4h; Inert atmosphere; | 99% |
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
benzaldehyde
(S)-2-(benzylideneamino)-4-methylsulfanylbutyric acid methyl ester
Conditions | Yield |
---|---|
Stage #1: (S)-methyl 2-amino-4-(methylthio)butanoate 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 120h; Reflux; | 90% |
With TEA; magnesium sulfate In tetrahydrofuran at 20℃; for 5h; |
N-(pyridin-2-yl)-N-methylcarbamoyl chloride
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
Conditions | Yield |
---|---|
With triethylamine In acetonitrile for 12h; Reflux; | 98% |
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
1-(tert-butoxy)-2-(tert-butoxy)carbonyl-1,2-dihydroisoquinoline
N-(tert-butoxycarbonyl)-L-methionine methyl ester
Conditions | Yield |
---|---|
In acetonitrile at 0℃; for 48h; | 97% |
In diethyl ether Heating; | 95% |
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
(3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid
(S)-tert-butyl 3-((S)-1-methoxy-4-(methylthio)-1-oxobutan-2-ylcarbamoyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate
Conditions | Yield |
---|---|
With 4-methyl-morpholine; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; pH=8 - 9; | 97% |
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 24h; | 97% |
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
Boc-Trp-OH
(S)-methyl 2-((S)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanamindo)-4-(methylthio)butanoate
Conditions | Yield |
---|---|
With N-ethylmorpholine;; (C3H7PO2)3 In dichloromethane; N,N-dimethyl-formamide for 25h; Ambient temperature; | 96% |
Stage #1: (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride With sodium carbonate In dichloromethane; water Stage #2: Boc-Trp-OH With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; | 65% |
With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 60% |
5-acetyl-2-chloro-3-nitrothiophene
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
(2S)-methyl (5-acetyl-3-nitro-2-thienyl)aminomethylsulfanylethylacetate
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 20℃; for 96h; | 96% |
furfural
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
(S)-2-(2-furylmethylideneamino)-4-methylsulfanylbutyric acid methyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 120h; Reflux; | 96% |
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
1-<(tert-butyloxy)carbonylamino>cyclopropane-1-carboxylic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 13h; | 96% |
Conditions | Yield |
---|---|
With potassium hexafluorophosphate; 4-methylpyridine-1-oxide; chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II); potassium carbonate In water; 1,2-dichloro-ethane at 37℃; for 24h; Inert atmosphere; Sealed tube; | 96% |
Conditions | Yield |
---|---|
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 dichloromethane at 20℃; for 5h; | 96% |
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
chloroacetyl chloride
2-(2-chloroacetylamino)-4-(methylsulfanyl)butyric acid methyl ester
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane; water at 0 - 20℃; | 95.2% |
phosgene
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
methyl (S)-2-isocyanato-4-(methylthio)butanoate
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran; dichloromethane at 0℃; for 2h; | 95% |
With pyridine In dichloromethane; toluene at 0℃; for 2h; |
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
4-nitro-2-(1-naphthyl)benzoic acid
N-[4-nitro-2-(1-naphthyl)benzoyl]-methionine methyl ester
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 10h; Acylation; | 95% |
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
1-deoxy-1-azido-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronic acid
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 24h; | 95% |
acetic anhydride
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
methyl N-acetylmethionine
Conditions | Yield |
---|---|
With pyridine at 20℃; Cooling with ice; | 94% |
With triethylamine In chloroform at 0℃; for 1h; |
(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride
(2S,4R)-1-(tert-butoxycarbonyl)-4-phenyl-2-pyrrolidinecarboxylic acid
(2S,4R)-2-((S)-1-Methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide Acylation; | 94% |
The Molecular Structure of L-Methionine methyl ester hydrochloride (CAS NO.2491-18-1):
Empirical Formula: C6H14ClNO2S
Molecular Weight: 199.6989
IUPAC Name: methyl 2-amino-4-methylsulfanylbutanoate hydrochloride
Appearance: Crystalline
Nominal Mass: 199 Da
Average Mass: 199.6989 Da
Monoisotopic Mass: 199.043376 Da
Flash Point: 121.7 °C
Melting Point: 151-153 °C
Enthalpy of Vaporization: 52.66 kJ/mol
Boiling Point: 277.6 °C at 760 mmHg
Vapour Pressure: 0.00345 mmHg at 25°C
Storage of L-Methionine methyl ester hydrochloride (CAS NO.2491-18-1): Store in a dry area. Keep refrigerated. (Store below 4°C/39°F.) Store in a tightly closed container. Keep container closed when not in use.
Synonyms: Methionine-ome hcl ; L-methionine methyl ester hydrochloride ; L-methionine methyl ester hydrochloride salt ; H-met-ome hcl ; H-met-ome hydrochloride ; Methyl l-methionate hydrochloride ; L-methionine methyl ester hcl ; H-met-ome.hcll-methionine methyl ester hydrochloride
Product Categories: Amino Acids;Methionine [Met, M];Amino Acids and Derivatives;Amino Acid Methyl Esters;Amino Acids (C-Protected);Biochemistry;Amino hydrochloride;Amino Acid Derivatives;Methionine;Peptide Synthesis
Safety: CAUTION: May irritate eyes, skin, and respiratory tract
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 24/25
S24/25: Avoid contact with skin and eyes
WGK Germany: 3
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