868-59-7

Basic information

• Product Name: L-Cysteine ethyl ester hydrochloride
• Synonyms: ethyl L-cysteinate hydrochloride;L-CYSTEINE ETHYL ESTER HYDROCHLORIDE, 98 % (99% EE/GLC);L-CYSTEINE ETHYL ESTER HYDROCHLORIDECRYS TALLINE;Cystanin;Cysteine, ethyl ester, hydrochloride, L- (6CI, 7CI, 8CI);Ethyl cysteinate hydrochloride;NSC 117387;NSC 519837
• CAS NO: 868-59-7
• Molecular Formula: C5H12ClNO2S
• Molecular Weight: 185.67
• EINECS: 212-779-6
• Product Categories: Amino Acids Derivatives;Cysteine [Cys, C];Amino Acids and Derivatives;Amino Acid Ethyl Esters;Amino Acids;Amino Acids (C-Protected);Biochemistry;Amino hydrochloride;Amino Acid Derivatives;Cysteine/Cystine;Peptide Synthesis
• Mol File: 868-59-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 123-125 °C(lit.)
• Boiling Point: 205.9 °C at 760 mmHg
• Flash Point: 78.3 °C
• Appearance: white/solid
• Density: 1.391 g/cm3
• Vapor Pressure: 0.244mmHg at 25°C
• Refractive Index: -11.5 ° (C=8, 1mol/L HCl)
• Storage Temp.: −20°C
• Water Solubility: Soluble in water.
• Sensitive: Hygroscopic
• BRN: 3562600
• CAS DataBase Reference: L-Cysteine ethyl ester hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: L-Cysteine ethyl ester hydrochloride(868-59-7)
• EPA Substance Registry System: L-Cysteine ethyl ester hydrochloride(868-59-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 2
• RTECS: HA1820000
• TSCA: Yes
• Hazardous Substances Data: 868-59-7(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

L-Cysteine ethyl ester hydrochloride is widely used in food additive, cosmetic, pharmaceutical area.

InChI:InChI=1/C5H11NO2S/c1-2-8-5(7)4(6)3-9/h4,9H,2-3,6H2,1H3/p+1/t4-/m0/s1

Synthetic route

ethanol (64-17-5) + L-Cysteine (52-90-4) → L-cysteine ethyl ester hydrochloride (868-59-7)

Conditions	Yield
With thionyl chloride for 15h; Cooling with ice; Reflux;	98.1%
With hydrogenchloride for 8h; Ambient temperature;
With thionyl chloride for 12h; Cooling with ice; Reflux;

L-Cysteine (52-90-4) → L-cysteine ethyl ester hydrochloride (868-59-7)

Conditions	Yield
	80%

ethanol (64-17-5) + l-cysteine hydrochloride → L-cysteine ethyl ester hydrochloride (868-59-7)

Conditions	Yield
With hydrogenchloride

ethanol (64-17-5) + l-cysteine hydrochloride (52-89-1) → L-cysteine ethyl ester hydrochloride (868-59-7)

Conditions	Yield
With hydrogenchloride at 40 - 50℃; for 8h;

ethyl Bromopyruvate (70-23-5) + L-cysteine ethyl ester hydrochloride (868-59-7) → diethyl (R)-3,4-dihydro-2H-1,4-thiazine-3,5-dicarboxylate (94110-58-4)

Conditions	Yield
With triethylamine In dichloromethane	100%

methyl 4-formylbutanoate (6026-86-4) + L-cysteine ethyl ester hydrochloride (868-59-7) → (R)-2-(3-Methoxycarbonyl-propyl)-thiazolidine-4-carboxylic acid ethyl ester (226888-62-6)

Conditions	Yield
With magnesium sulfate; potassium carbonate In toluene Ambient temperature;	100%

L-cysteine ethyl ester hydrochloride (868-59-7) + 2-oxopropanal (78-98-8) → 2-acetyl-4-ethoxycarbonylthiazolidine

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 20℃; for 12h;	100%
With sodium hydrogencarbonate In ethanol; water at 20℃; for 18h; Inert atmosphere;
With sodium hydrogencarbonate In ethanol; water
With sodium hydrogencarbonate In ethanol; water at 20℃; for 18h;

dichloroacetonitrile (3018-12-0) + L-cysteine ethyl ester hydrochloride (868-59-7) → ethyl 2-(chloromethyl)thiazole-4-carboxylate (842130-48-7)

Conditions	Yield
Stage #1: dichloroacetonitrile With sodium methylate In methanol; dichloromethane at 0℃; for 1h; Inert atmosphere; Stage #2: L-cysteine ethyl ester hydrochloride In methanol; dichloromethane at 25℃; for 12h; Inert atmosphere; Stage #3: With N-ethyl-N,N-diisopropylamine In dichloromethane at 25 - 50℃; for 17h; Inert atmosphere;	100%

2,3-dimethyl-2,3-butane diol (76-09-5) + (3-chloroprop-1-en-1-yl)boronic acid (215951-86-3) + L-cysteine ethyl ester hydrochloride (868-59-7) + trifluoroacetic acid (76-05-1) → C14H26BNO4S*C2HF3O2

Conditions	Yield
Stage #1: 2,3-dimethyl-2,3-butane diol; (3-chloroprop-1-en-1-yl)boronic acid; L-cysteine ethyl ester hydrochloride With caesium carbonate; sodium iodide In N,N-dimethyl-formamide at 20℃; for 4h; Stage #2: trifluoroacetic acid In acetonitrile	100%

L-cysteine ethyl ester hydrochloride (868-59-7) + 3-hydroxy-1-(2,6,6-trimethylcyclohex-3-en-1-yl)but-2-en-1-one → ethyl N-(4-oxo-4-(2,6,6-trimethylcyclohex-3-en-1-yl)but-2-en-2-yl)cysteinate

Conditions	Yield
With acetic acid In toluene Reflux; Dean-Stark;	100%

Togni's reagent (887144-97-0) + L-cysteine ethyl ester hydrochloride (868-59-7) → (R)-ethyl 2-amino-3-((trifluoromethyl)thio)propanoate hydrochloride

Conditions	Yield
In methanol	99%
In methanol at -78 - 20℃; for 1h; Schlenk technique; Inert atmosphere;	97%

L-cysteine ethyl ester hydrochloride (868-59-7) + ethyl benzimidate hydrochloride (5333-86-8) → Ethyl 5,5-dihydro-2-phenyl-2-thiazoline-4-carboxylate (70454-09-0)

Conditions	Yield
With triethylamine In methanol at 20℃;	99%

pyridine-2-carbaldehyde (1121-60-4) + L-cysteine ethyl ester hydrochloride (868-59-7) → (R,S)-ethyl-2-(pyridin-2-yl-)thiazolidine-4-(R)-carboxylate (189228-41-9)

Conditions	Yield
With potassium hydrogencarbonate In methanol; water at 20℃; Inert atmosphere;	99%
With potassium hydrogencarbonate In methanol; water

L-cysteine ethyl ester hydrochloride (868-59-7) + 4-(pyridin-4-yl)benzaldehyde (99163-12-9) → (R,S)-ethyl-2-(4-(pyridin-4-yl)-phenyl)-thiazolidine-4-(R)-carboxylate (1263098-05-0)

Conditions	Yield
With potassium hydrogencarbonate In methanol; water at 20℃; Inert atmosphere;	99%
With potassium hydrogencarbonate In methanol; water

L-cysteine ethyl ester hydrochloride (868-59-7) → L-cystine diethyl ester (583-89-1)

Conditions	Yield
With bromopentacarbonylmanganese(I); oxygen In water-d2; tert-butyl alcohol at 20℃; for 5h; UV-irradiation; chemoselective reaction;	99%
In dimethyl sulfoxide at 30℃; for 5h; Kinetics; Thermodynamic data; Solvent; Temperature;

L-cysteine ethyl ester hydrochloride (868-59-7) + benzaldehyde (100-52-7) → 2-phenylthiazolidine-4-carboxylic acid ethyl ester

Conditions	Yield
With tert.-butylhydroperoxide; iodine; potassium carbonate In 1,4-dioxane at 70℃; for 1.5h; Schlenk technique; Inert atmosphere;	99%

ethyl acetimidate hydrochloride (2208-07-3) + L-cysteine ethyl ester hydrochloride (868-59-7) → ethyl 2-methyl-2-thiazoline-(4R)-carboxylate (89530-18-7)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	98%
With triethylamine In dichloromethane at 0℃; Condensation;	85%

L-cysteine ethyl ester hydrochloride (868-59-7) + (2S)-2-[N-(tert-butoxycarbonyl)amino]-1-iodo-4-methylpentane (161529-19-7) → ethyl (2R)-2-amino-3-{(2'S)-2'-[(tert-butoxycarbonyl)amino]-4'-methylpentylthio}propanoate (876297-28-8)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	98%

di-tert-butyl dicarbonate (24424-99-5) + L-cysteine ethyl ester hydrochloride (868-59-7) → N-Boc-L-cysteine ethyl ester (118143-52-5)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 2h;	98%
Stage #1: L-cysteine ethyl ester hydrochloride With sodium hydrogencarbonate In dichloromethane at -5℃; for 0.166667h; Stage #2: di-tert-butyl dicarbonate In dichloromethane at -5 - 20℃;	98%
With triethylamine In tetrahydrofuran
With triethylamine In tetrahydrofuran at 0 - 20℃;

ethyl (R)-2-(tert-butoxycarbonylamino)-3-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfanyl]propanoate (1002347-44-5) + L-cysteine ethyl ester hydrochloride (868-59-7) → ethyl (R)-2-amino-3-{[(R)-2-(tert-butoxycarbonylamino)-2-(ethoxycarbonyl)ethyl]disulfanyl}propanoate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.25h;	98%

L-cysteine ethyl ester hydrochloride (868-59-7) + benzyl chloroformate (501-53-1) → N-(benzyloxycarbonyl)-L-cysteine ethyl ester (95084-26-7)

Conditions	Yield
Stage #1: L-cysteine ethyl ester hydrochloride With sodium hydrogencarbonate In dichloromethane at -5℃; for 0.166667h; Stage #2: benzyl chloroformate In dichloromethane at -5 - 20℃;	98%

p-ethoxycarbonylbenzaldehyde (6287-86-1) + L-cysteine ethyl ester hydrochloride (868-59-7) → (R,S)-ethyl-2-[4-(methoxycarbonyl)phenyl]-thiazolidine-4-(R)-carboxylate (1263098-07-2)

Conditions	Yield
With potassium hydrogencarbonate In methanol; water at 20℃; Inert atmosphere;	98%
With potassium hydrogencarbonate In methanol; water

L-cysteine ethyl ester hydrochloride (868-59-7) + (2S)-2-[N-(tert-butoxycarbonyl)amino]-1-iodo-3-phenylpropane (154669-56-4) → ethyl (2R)-2-amino-3-{(2'S)-2'-[(tert-butyloxycarbonyl)amino]-3'-phenylpropylthio}propanoate (876297-27-7)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	97%

11-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfanyl]undecanoic acid (1002347-32-1) + L-cysteine ethyl ester hydrochloride (868-59-7) → ethyl (R)-2-amino-3-[(10-carboxydecyl)disulfanyl]propanoate hydrochloride (1002348-03-9)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.25h;	97%

L-cysteine ethyl ester hydrochloride (868-59-7) + (S)-2-iodomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (338945-22-5) → ethyl (2R)-2-amino-3-{[(2'S)-1-(tert-butoxycarbonyl)pyrrolidin-2'-yl]methylthio}propanoate (876297-29-9)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	96%

L-cysteine ethyl ester hydrochloride (868-59-7) + dimethyl N-cyanodithioiminocarbonate (10191-60-3) → (R)-2-[(Z)-Cyanoimino]-thiazolidine-4-carboxylic acid ethyl ester (258822-90-1)

Conditions	Yield
With triethylamine In ethanol Cyclization;	95%

L-cysteine ethyl ester hydrochloride (868-59-7) + ethyl benzimidate hydrochloride (5333-86-8) → (4R)-ethyl 2-phenyl-4,5-dihydrothiazole-4-carboxylate (89530-19-8)

Conditions	Yield
With triethylamine In methanol at 20℃; for 0.18h; Inert atmosphere;	95%
With triethylamine In ethanol for 2h; Heating;	87%

L-cysteine ethyl ester hydrochloride (868-59-7) + p-benzoquinone (106-51-4) → ethyl (R)-2-amino-3-(2,5-dihydroxyphenylsulfanyl)propanoate hydrochloride (389135-53-9)

Conditions	Yield
In methanol at 20℃; for 1h; Inert atmosphere;	95%
In methanol; water at 20℃; for 1h;

L-cysteine ethyl ester hydrochloride (868-59-7) + allyl α-D-mannopyranoside (41308-76-3) → S-[3-(α-D-mannopyranosyloxy)propyl]-L-cysteine ethyl ester (1259301-27-3)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In 1,4-dioxane at 65℃; for 4h; Inert atmosphere; chemoselective reaction;	95%

L-cysteine ethyl ester hydrochloride (868-59-7) + 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one → (R)-ethyl 2-amino-3-(((triisopropylsilyl)ethynyl)thio)propanoate (1443746-67-5)

Conditions	Yield
Stage #1: L-cysteine ethyl ester hydrochloride With N,N,N',N'-tetramethylguanidine In tetrahydrofuran; water at 20℃; for 0.0833333h; Stage #2: 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one In tetrahydrofuran; water at 20℃; for 0.0833333h; chemoselective reaction;	95%

C33H32N4O8 (1610426-90-8) + L-cysteine ethyl ester hydrochloride (868-59-7) → C43H50N6O10S2 (1610426-81-7)

Conditions	Yield
With chloroformic acid ethyl ester; triethylamine In dichloromethane at 0℃; for 0.25h;	95%

L-cysteine ethyl ester hydrochloride (868-59-7) + 3-methoxy-benzaldehyde (591-31-1) → ethyl 2-(3-methoxyphenyl)thiazole-4-carboxylate (115299-08-6)

Conditions	Yield
With tert.-butylhydroperoxide; iodine; potassium carbonate In 1,4-dioxane at 70℃; for 12h; Schlenk technique; Molecular sieve; Inert atmosphere;	95%

1-(2,6,6-trimethyl-3-cyclo-hexen-1-yl)-2-buten-1-one (359865-01-3) + L-cysteine ethyl ester hydrochloride (868-59-7) → ethyl S-(4-oxo-4-(2’.6’.6’-trimethylcyclohex-3’-en-1’-yl)butan-2-yl)-L-cysteinate

Conditions	Yield
With potassium carbonate In water at 20℃;	95%

Upstream product

• 64-17-5 ethanol 
• 52-90-4 L-Cysteine 
• 52-89-1 l-cysteine hydrochloride 

Downstream Products

• 19040-22-3 (R)-2-(benzyloxycarbonylamino-methyl)-4,5-dihydro-thiazole-4-carboxylic acid ethyl ester 
• 1791-59-9 5-phenyl-2,3-dihydro-thiazolo[3,2-c]quinazoline-3,10b-dicarboxylic acid 3-ethyl ester 
• 17337-88-1 (R)-2-((S)-1-benzyloxycarbonylamino-ethyl)-4,5-dihydro-thiazole-4-carboxylic acid ethyl ester 
• 17330-31-3 (R)-2-((S)-1-benzyloxycarbonylamino-2-methyl-propyl)-4,5-dihydro-thiazole-4-carboxylic acid ethyl ester 
• 17330-32-4 (R)-2-((S)-1-benzyloxycarbonylamino-3-methyl-butyl)-4,5-dihydro-thiazole-4-carboxylic acid ethyl ester 
• 17330-33-5 (R)-2-((1S,2S)-1-benzyloxycarbonylamino-2-methyl-butyl)-4,5-dihydro-thiazole-4-carboxylic acid ethyl ester 
• 802852-89-7 S-[(Ξ)-1-(4-benzothiazol-2-yl-phenyl)-2,5-dioxo-pyrrolidin-3-yl]-L-cysteine ethyl ester 
• 60664-15-5 ethyl (4R)-1,3-thiazolidine-4-carboxylate 
• 27486-86-8 S-trityl-L-cysteinate d'ethyle 
• 116987-46-3 -2 methyl-2 thiazolidine carboxylate d'ethyle-4 (R) 
• 99876-71-8 ethyl 2-(4-chloro-3-sulfamylphenyl)-4(R)-thiazolidinecarboxylate 
• 135673-76-6 ethyl 2-(4-ethoxycarbonyl-2-thiazolinylidene)benzoylacetate 
• 70454-09-0 Ethyl 5,5-dihydro-2-phenyl-2-thiazoline-4-carboxylate 
• 91641-78-0 N-benzoyl-L-cysteine ethyl ester 

Relevant articles and documents

Benzo thiazole carboxamides and application thereof

The invention belongs to the technical field of medicines and relates to a benzothiazole formamide compound and application thereof. The benzothiazole formamide compound comprises a derivative of the benzothiazole formamide compound and pharmaceutically applicable salt; a general molecular formula is shown in the description, wherein R1, R2 and Ar are described as claims and the description. The benzothiazole formamide compound and addition salt of the pharmaceutically applicable acid of the compound can be combined with an existing medicine or can be independently utilized as an epidermal growth factor tyrosine kinase inhibitor for treating related diseases of epidermal growth factor acceptor signal transduction disorder, such as small cell lung cancer, squamous cancer, glandular cancer, large cell lung cancer, colorectal cancer, breast cancer, ovarian cancer and renal cell carcinoma. A formula is shown in the description.

Novel thiazolidine derivatives as chiral catalysts in the enantioselective addition of diethylzinc to aldehydes

New chiral thiazolidine derivatives were synthesized conveniently from natural L-cysteine and showed good enantioselectivity (up to 90% ee) in the addition of diethylzinc to aldehydes. The catalytic efficiency of the thiazolidine derivatives is influenced by the different structures of the thiazolidine rings and the bulkiness of R moiety in the ester groups. (C) 2000 Elsevier Science Ltd.

Convenient synthesis of 1,4-thiazane-3-carboxylic acid derivatives

-