Methyl L-DOPA HCl | L-3,4-Dihydroxyphenylalanine methyl ester hydrochloride | Amines

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Quality Control of Methyl L-DOPA HCl Purity: 95% SDS Specification

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NMR

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Product Details of Methyl L-DOPA HCl

CAS No. :	1421-65-4
Formula :	C₁₀H₁₄ClNO₄
M.W :	247.68
SMILES Code :	O=C(OC)[C@@H](N)CC1=CC=C(O)C(O)=C1.[H]Cl
Synonyms :	L-3,4-Dihydroxyphenylalanine methyl ester hydrochloride; Melevodopa hydrochloride
MDL No. :	MFCD00038958
InChI Key :	WFGNJLMSYIJWII-FJXQXJEOSA-N
Pubchem ID :	10131132

Safety of Methyl L-DOPA HCl

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of Methyl L-DOPA HCl

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1421-65-4 ]

[ 1421-65-4 ] Synthesis Path-Downstream 1~35

1
[ 67561-03-9 ]
[ 1421-65-4 ]
[ 880262-98-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1282 - 1285.

2
[ 60656-87-3 ]
[ 1421-65-4 ]
[ 880262-24-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1282 - 1285.

3
[ 1421-65-4 ]
[ 145525-27-5 ]
7,8-dihydroxy-1,2,3,4,3',4'-hexahydro-1'H-[1,3']biisoquinolinyl-3,2'-dicarboxylic acid 2'-tert-butyl ester 3-methyl ester [ No CAS ]
6,7-dihydroxy-1,2,3,4,3',4'-hexahydro-1'H-[1,3']biisoquinolinyl-3,2'-dicarboxylic acid 2'-tert-butyl ester 3-methyl ester [ No CAS ]
[ 879287-96-4 ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 1319 - 1323.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2598 - 2602.

4
[ 1421-65-4 ]
[ 77-78-1 ]
[ 145525-27-5 ]
[ 879288-01-4 ]
[ 879288-00-3 ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 1319 - 1323.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2598 - 2602.

5
[ 1421-65-4 ]
[ 1200-22-2 ]
(S)-3-(3,4-Dihydroxy-phenyl)-2-((R)-5-[1,2]dithiolan-3-yl-pentanoylamino)-propionic acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1486 - 1493.

6
[ 1421-65-4 ]
[ 100-52-7 ]
C₁₇H₁₇NO₄ [ No CAS ]

References: [1]Synlett,2006,p. 1903 - 1907.

7
[ 1421-65-4 ]
[ 100-52-7 ]
C₁₇H₁₇NO₄ [ No CAS ]
C₁₅H₁₃NO₂ [ No CAS ]

References: [1]Synlett,2006,p. 1903 - 1907.

8
[ 331-39-5 ]
[ 1421-65-4 ]
[ 120094-83-9 ]

Yield	Reaction Conditions	Operation in experiment
40%		Caffeic acid (140.7 mg, 0.78 mmol) was dissolved in CH2Cl2/DMF (1:3, 3.0 mL), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide(EDC) (247 mL, 147 mmol) and 1-hydroxy-benzotriazole(HOBt) (75.4 mg, 0.56 mmol) were added to the solution. After themixture was cooled in an ice-water bath for 15 min, Et3N (156 mL,1.12 mmol) and compound a (138.3 mg, 0.56 mmol) were added tothe mixture. After stirring at room temperature for 19 h, the mixturewas poured into H2O (50 mL), extracted with EtOAc (50 mL 3), washed with 5% NaHCO3 (150 mL) and brine (150 mL), driedover MgSO4, filtered, and the solvent removed in vacuo. The residue was purified by silica gel column chromatography (CHCl3:MeOH =9:1) to afford clovamide methyl ester (clovamide-Me, 10, 84.7 mg,40%) as a yellow powder: 1H NMR (CD3OD) d 7.36 (1H, d, J = 15.7Hz, H-70), 6.99 (1H, d, J = 1.9 Hz, H-2), 6.89 (1H, dd, J = 8.2, 1.9 Hz,H-6), 6.75 (1H, d, J = 8.2 Hz, H-5), 6.64 (1H, d, J = 1.9 Hz, H-20),6.67 (1H, d, J = 8.1 Hz, H-50), 6.53 (1H, dd, J = 8.1, 1.9 Hz, H-60),6.41 (1H, d, J = 15.7 Hz, H-80), 4.69 (1H, m, H-8), 3.68 (3H, s,MeO-90), 3.02 (1H, dd, J = 13.9, 5.9 Hz, H-7a), 2.93 (1H, dd, J =13.9, 6.6 Hz, H-7b); 13C NMR (CD3OD) d 174.6 (C, C-9), 169.8(C, C-90), 149.5 (C, C-40), 147.3 (C, C-30), 146.8 (C, C-3), 145.9(C, C-4), 143.8 (CH, C-70), 130.2 (C, C-1), 128.9 (C, C-10), 123.1(CH, C-60), 122.4 (CH, C-6), 118.4 (CH, C-80), 118.0 (CH, C-2),117.2 (CH, C-5), 117.1 (CH, C-50), 115.9 (CH, C-20), 56.5 (CH, C-8),53.4 (CH3, CO-9) 39.1 (C, C-7); UV kmax (MeOH) nm (e): 208(12400), 220 (12100), 291 (9700), 324 (10700); HR-ESI-MS (negativeion) m/z: 372.1100 [MH] (calcd for C19H18NO7, 372.1083);[a]D20 +20 (c = 1.0, MeOH).
33.2%		General procedure: To a solution of the corresponding substitutedacid (1 eq, 2.02 mmol) in dichloromethane-N,N-dimethylformamide(DMF) (3 : 1, 20 mL) was added 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) (1 eq, 2.02 mmol),N,N-diisopropylethylamine (DIEA) (1 eq, 2.02 mmol) andN-hydroxybenzotriazole (HOBt) (1 eq, 2.02 mmol). After themixture was stirred at room temperature for 30 min, correspondingamine (1 eq, 2.02 mmol) and triethylammoniumacetate (TEA) (3 eq, 6.06 mmol) was added. The solution wasstirred at room temperature for 4 h and then extracted withdichloromethane. The organic layer was washed with 1 N HClsolution, saturated NaHCO3 solution, water and brine, driedover Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel column chromatography (ethylacetate-hexane, 1 : 2) to obtain the title compound.
	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃;	General procedure: As shown in Scheme 1, the synthetic route of the analogues (1-7) involved a two-step sequence viamethyl esterification of L-amino acidand amide condensation. 100 muL SOCl2was added in portions to 4 mL methanol at -10 C,then 1 mmol L-amino acid was addedand the mixture was warmed to room temperature and stirred overnight. After thesolvent was removed, 5 mL CH3CN, 500 muL DIPEA (N,N-Diisopropyl ethylamine), 1.1 mmolcorresponding substituted acid and 1.1 mmol HBTU (O-Benzotriazole-N,N,N',N'-tetramethyl-uronium-hexafluorophosphate)was added into the residue. The mixture was stirred for 1 h at room temperatureto finish condensation. The reaction solution was added 20 mL 1 M HCl, andextracted with ethyl acetate (4 × 20 mL). The combined organic phasewas dried over anhydrous Na2SO4 and finally evaporated invacuum. The residue was purified by silica-gel chromatography using mixtures ofPE/EtOAcas eluent to afford compounds 1-7.At this stage, all compounds were fully analyzed and characterized by nuclearmagnetic resonance (NMR), high resolution massspectrum (HRMS).

References: [1]European Journal of Medicinal Chemistry,2007,vol. 42,p. 1309 - 1315.
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 3202 - 3209.
[3]Biological and Pharmaceutical Bulletin,2017,vol. 40,p. 1475 - 1482.
[4]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 302 - 312.

9
[ 1421-65-4 ]
[ 879288-05-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2598 - 2602.

10
[ 1421-65-4 ]
C₂₂H₂₆N₂O₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2598 - 2602.

11
[ 1421-65-4 ]
[ 879288-06-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2598 - 2602.

12
[ 1421-65-4 ]
[ 879288-08-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2598 - 2602.

13
[ 1421-65-4 ]
[ 879288-02-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2598 - 2602.

14
[ 1421-65-4 ]
[ 879287-99-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2598 - 2602.

15
[ 1421-65-4 ]
C₂₂H₂₆N₂O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2598 - 2602.

16
[ 1421-65-4 ]
C₂₃H₂₉N₃O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2598 - 2602.

17
[ 1421-65-4 ]
C₃₁H₃₁N₃O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2598 - 2602.

18
[ 1421-65-4 ]
C₃₃H₃₃F₅N₂O₆ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2598 - 2602.

19
[ 1421-65-4 ]
[ 880262-32-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1282 - 1285.

20
[ 1421-65-4 ]
[ 880262-28-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1282 - 1285.

21
[ 1421-65-4 ]
[ 880262-26-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1282 - 1285.

22
[ 1421-65-4 ]
[ 880263-02-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1282 - 1285.

23
[ 1421-65-4 ]
[ 880263-00-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1282 - 1285.

24
[ 1421-65-4 ]
[ 880262-99-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1282 - 1285.

25
[ 1421-65-4 ]
C₂₅H₃₂N₂O₆ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1282 - 1285.

26
[ 1421-65-4 ]
[ 880262-43-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1282 - 1285.

27
[ 1421-65-4 ]
[ 880262-77-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1282 - 1285.

28
[ 1421-65-4 ]
[ 880262-45-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1282 - 1285.

29
[ 1421-65-4 ]
C₂₈H₃₃N₃O₆ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1282 - 1285.

30
[ 1421-65-4 ]
[ 880262-39-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1282 - 1285.

31
[ 1421-65-4 ]
(1R,3S)-1-Benzyloxymethyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester; hydrochloride [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1282 - 1285.

32
[ 1421-65-4 ]
C₂₈H₃₅N₃O₆ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1282 - 1285.

33
[ 1421-65-4 ]
[ 880262-85-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1282 - 1285.

34
[ 1421-65-4 ]
[ 880262-41-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1282 - 1285.

35
[ 1421-65-4 ]
C₂₉H₃₃N₃O₆ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1282 - 1285.

Historical Records

Technical Information

• Acidity of Phenols • Acyl Group Substitution • Alkyl Halide Occurrence • Bouveault-Blanc Reduction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Electrophilic Substitution of the Phenol Aromatic Ring • Ester Cleavage • Etherification Reaction of Phenolic Hydroxyl Group • Halogenation of Phenols • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Oxidation of Phenols • Pechmann Coumarin Synthesis • Petasis Reaction • Preparation of Aldehydes and Ketones • Preparation of Amines • Reactions of Amines • Reactions with Organometallic Reagents • Reimer-Tiemann Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

Precautionary Statements-General
Code	Phrase
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Code	Phrase
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Response
Code	Phrase
P301	IF SWALLOWED:
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P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
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P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
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P337	If eye irritation persists:
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P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
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P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
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P405	Store locked up.
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P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 1421-65-4

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CAS No.: 1421-65-4

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Product Details of Methyl L-DOPA HCl

Safety of Methyl L-DOPA HCl

Application In Synthesis of Methyl L-DOPA HCl

[ 1421-65-4 ] Synthesis Path-Downstream 1~35

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