Product Name

  • Name

    ALPHA-METHYL-L-P-TYROSINE

  • EINECS 211-599-5
  • CAS No. 672-87-7
  • Article Data7
  • CAS DataBase
  • Density 1.283g/cm3
  • Solubility
  • Melting Point 320-340°C dec.
  • Formula C10H13 N O3
  • Boiling Point 383.7oC at 760 mmHg
  • Molecular Weight 195.218
  • Flash Point 185.9oC
  • Transport Information
  • Appearance White Solid
  • Safety 2368400
  • Risk Codes 2368400
  • Molecular Structure Molecular Structure of 672-87-7 (ALPHA-METHYL-L-P-TYROSINE)
  • Hazard Symbols
  • Synonyms Tyrosine,a-methyl-, L- (8CI);(S)-2-(4-Hydroxybenzyl)-2-aminopropanoic acid; (S)-a-Methyltyrosine; Demser; L(-)-Metyrosine;L-Metyrosine; L-a-MT;L-a-Methyl-p-tyrosine; L-a-Methyltyrosine; MK 781;Metirosine; Metyrosine; a-Methyl-L-tyrosine
  • PSA 83.55000
  • LogP 1.43700

Synthetic route

(2S)-2-amino-3-(4-methoxyphenyl)-2-methyl-propionamide hydrogen bromide salt
1299492-19-5

(2S)-2-amino-3-(4-methoxyphenyl)-2-methyl-propionamide hydrogen bromide salt

L-methyltyrosine
672-87-7

L-methyltyrosine

Conditions
ConditionsYield
With water; hydrogen bromide at 105℃; for 17h; Product distribution / selectivity;86%
2-(S)-amino-3-(4-methoxyphenyl)-2-methylpropionamide
1299492-09-3

2-(S)-amino-3-(4-methoxyphenyl)-2-methylpropionamide

L-methyltyrosine
672-87-7

L-methyltyrosine

Conditions
ConditionsYield
With water; hydrogen bromide at 120℃; for 5h; Product distribution / selectivity;84%
Multi-step reaction with 2 steps
1: water; hydrogen bromide / methanol / 100 °C / 15 - 22.5 Torr
2: water; hydrogen bromide / 17 h / 105 °C
View Scheme
(2S)-2-amino-3-(4-methoxyphenyl)-2-methyl-propionamide hydrochloride
1299492-14-0

(2S)-2-amino-3-(4-methoxyphenyl)-2-methyl-propionamide hydrochloride

L-methyltyrosine
672-87-7

L-methyltyrosine

Conditions
ConditionsYield
With hydrogen bromide In water at 120℃; for 4h; Product distribution / selectivity;83%
(2S)-2-amino-3-(4-methoxyphenyl)-2-methylpropionamide formic acid salt
1299492-20-8

(2S)-2-amino-3-(4-methoxyphenyl)-2-methylpropionamide formic acid salt

L-methyltyrosine
672-87-7

L-methyltyrosine

Conditions
ConditionsYield
With water; hydrogen bromide at 105℃; for 17h; Product distribution / selectivity;82%
(S)-N2-benzoyl-O4',2-dimethyltyrosine

(S)-N2-benzoyl-O4',2-dimethyltyrosine

L-methyltyrosine
672-87-7

L-methyltyrosine

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane at 100℃; for 4h;75.4%
tert-butyl (2R)-2-amino-3-(4-methoxyphenyl)-2-methylpropanoate

tert-butyl (2R)-2-amino-3-(4-methoxyphenyl)-2-methylpropanoate

L-methyltyrosine
672-87-7

L-methyltyrosine

Conditions
ConditionsYield
Stage #1: tert-butyl (2R)-2-amino-3-(4-methoxyphenyl)-2-methylpropanoate With boron tribromide In dichloromethane at 20℃; for 1.5h;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water Product distribution / selectivity;
45.4%
N-Chloroacetyl-α-methyltyrosine
121703-96-6

N-Chloroacetyl-α-methyltyrosine

A

L-methyltyrosine
672-87-7

L-methyltyrosine

B

α-methyl-D-tyrosine
672-86-6

α-methyl-D-tyrosine

C

N-Chloroacetyl-D-α-methyltyrosine
121704-37-8

N-Chloroacetyl-D-α-methyltyrosine

D

N-Chloroacetyl-L-α-methyltyrosine
121703-96-6, 121704-37-8

N-Chloroacetyl-L-α-methyltyrosine

Conditions
ConditionsYield
With potassium hydroxide; porcine kidney acylase I pH 7.5-8.0; Yields of byproduct given;A 30%
B n/a
C n/a
D n/a
With potassium hydroxide; porcine kidney acylase I pH 7.5-8.0; Yields of byproduct given;A n/a
B 30%
C n/a
D n/a
With potassium hydroxide; porcine kidney acylase I pH 7.5-8.0; Yield given. Yields of byproduct given;
α-methyl-β-p-methoxyphenyl-alanine
65555-88-6

α-methyl-β-p-methoxyphenyl-alanine

L-methyltyrosine
672-87-7

L-methyltyrosine

Conditions
ConditionsYield
With hydrogen bromide
N-Chloroacetyl-α-methyltyrosine
121703-96-6

N-Chloroacetyl-α-methyltyrosine

A

L-methyltyrosine
672-87-7

L-methyltyrosine

B

N-Chloroacetyl-D-α-methyltyrosine
121704-37-8

N-Chloroacetyl-D-α-methyltyrosine

Conditions
ConditionsYield
With potassium hydroxide; potassium phosphate buffer; porcine kidney acylase I at 40℃; relative initial rate of hydrolysis, also with Aspergillus acylase I as a catalyst; with or without CoCl2;
2-Nitro-2-(4-hydroxybenzyl)propionsaeureethylester
16109-65-2

2-Nitro-2-(4-hydroxybenzyl)propionsaeureethylester

L-methyltyrosine
672-87-7

L-methyltyrosine

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide; nickel 1.) MeOH, reflux, 1 h, 2.) MeOH, 28 h; Yield given. Multistep reaction;
(4-hydroxyphenyl)methanol
623-05-2

(4-hydroxyphenyl)methanol

L-methyltyrosine
672-87-7

L-methyltyrosine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 56.1 percent / tetrabutylammonium chloride, potassium fluoride dihydrate / toluene / 48 h / Heating
2: 2.) H2 / 1.) Raney-Ni, 2.) PtO2 / 1.) MeOH, reflux, 1 h, 2.) MeOH, 28 h
View Scheme
p-Methoxybenzyl bromide
2746-25-0

p-Methoxybenzyl bromide

L-methyltyrosine
672-87-7

L-methyltyrosine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: NaH / tetrahydrofuran / 0 - 25 °C
2: α-chymotrypsin / dimethylsulfoxide; H2O / 22 - 25 °C / potassium phosphate ( pH 7.0); with pig liver esterase the reaction rate is higher but the e.e. is lower
3: 1.) acyl azide formation, 2.) Curtius rearrangement
4: aq. HBr (48 percent)
View Scheme
2-<(4-methoxyphenyl)methyl>-2-methylpropanedioic acid, dimethyl ester
21118-89-8

2-<(4-methoxyphenyl)methyl>-2-methylpropanedioic acid, dimethyl ester

L-methyltyrosine
672-87-7

L-methyltyrosine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: α-chymotrypsin / dimethylsulfoxide; H2O / 22 - 25 °C / potassium phosphate ( pH 7.0); with pig liver esterase the reaction rate is higher but the e.e. is lower
2: 1.) acyl azide formation, 2.) Curtius rearrangement
3: aq. HBr (48 percent)
View Scheme
(R)-2-(4-Methoxy-benzyl)-2-methyl-malonic acid monomethyl ester
21186-54-9

(R)-2-(4-Methoxy-benzyl)-2-methyl-malonic acid monomethyl ester

L-methyltyrosine
672-87-7

L-methyltyrosine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) acyl azide formation, 2.) Curtius rearrangement
2: aq. HBr (48 percent)
View Scheme
4-methoxybenzyl methyl ketone
122-84-9

4-methoxybenzyl methyl ketone

L-methyltyrosine
672-87-7

L-methyltyrosine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: water; methanol / 20 h / 40 °C / Sealed tube
2.1: sulfuric acid / dichloromethane; water / 3.25 h / -10 - 0 °C / Cooling with ice
2.2: pH 8 - 9
3.1: ammonium formate / palladium on carbon / isopropyl alcohol / 1 h / Inert atmosphere; Reflux
4.1: water; hydrogen bromide / methanol / 100 °C / 15 - 22.5 Torr
5.1: water; hydrogen bromide / 17 h / 105 °C
View Scheme
Multi-step reaction with 4 steps
1.1: water; methanol / 20 h / 40 °C / Sealed tube
2.1: sulfuric acid / dichloromethane; water / 3.25 h / -10 - 0 °C / Cooling with ice
2.2: pH 8 - 9
3.1: palladium on carbon / water; methanol / 5.75 h / 20 - 60 °C
4.1: water; hydrogen bromide / 17 h / 105 °C
View Scheme
Multi-step reaction with 4 steps
1.1: water; methanol / 20 h / 40 °C / Sealed tube
2.1: sulfuric acid / dichloromethane; water / 3.25 h / -10 - 0 °C / Cooling with ice
2.2: pH 8 - 9
3.1: ammonium formate / palladium on carbon / isopropyl alcohol / 1 h / Inert atmosphere; Reflux
4.1: water; hydrogen bromide / 5 h / 120 °C
View Scheme
2-[1-(S)-cyano-2-(4-methoxyphenyl)-1-methylethylamino]-2-(R)-phenylacetamide
1299492-07-1

2-[1-(S)-cyano-2-(4-methoxyphenyl)-1-methylethylamino]-2-(R)-phenylacetamide

L-methyltyrosine
672-87-7

L-methyltyrosine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sulfuric acid / dichloromethane; water / 3.25 h / -10 - 0 °C / Cooling with ice
1.2: pH 8 - 9
2.1: ammonium formate / palladium on carbon / isopropyl alcohol / 1 h / Inert atmosphere; Reflux
3.1: water; hydrogen bromide / methanol / 100 °C / 15 - 22.5 Torr
4.1: water; hydrogen bromide / 17 h / 105 °C
View Scheme
Multi-step reaction with 3 steps
1.1: sulfuric acid / dichloromethane; water / 3.25 h / -10 - 0 °C / Cooling with ice
1.2: pH 8 - 9
2.1: palladium on carbon / water; methanol / 5.75 h / 20 - 60 °C
3.1: water; hydrogen bromide / 17 h / 105 °C
View Scheme
Multi-step reaction with 3 steps
1.1: sulfuric acid / dichloromethane; water / 3.25 h / -10 - 0 °C / Cooling with ice
1.2: pH 8 - 9
2.1: ammonium formate / palladium on carbon / isopropyl alcohol / 1 h / Inert atmosphere; Reflux
3.1: water; hydrogen bromide / 5 h / 120 °C
View Scheme
2-[(R)-(carbamoylphenylmethyl)-amino]-3-(4-methoxyphenyl)-2-(S)-methylpropionamide
1299492-08-2

2-[(R)-(carbamoylphenylmethyl)-amino]-3-(4-methoxyphenyl)-2-(S)-methylpropionamide

L-methyltyrosine
672-87-7

L-methyltyrosine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ammonium formate / palladium on carbon / isopropyl alcohol / 1 h / Inert atmosphere; Reflux
2: water; hydrogen bromide / methanol / 100 °C / 15 - 22.5 Torr
3: water; hydrogen bromide / 17 h / 105 °C
View Scheme
Multi-step reaction with 2 steps
1: ammonium formate / palladium on carbon / isopropyl alcohol / 1 h / Inert atmosphere; Reflux
2: water; hydrogen bromide / 5 h / 120 °C
View Scheme
Multi-step reaction with 2 steps
1: palladium on carbon / water; methanol / 5.75 h / 20 - 60 °C
2: water; hydrogen bromide / 17 h / 105 °C
View Scheme
3-(4-methoxyphenyl)-2-methyl-2-((S)-1-phenyl-ethylamino)-propionamide
1299492-11-7

3-(4-methoxyphenyl)-2-methyl-2-((S)-1-phenyl-ethylamino)-propionamide

L-methyltyrosine
672-87-7

L-methyltyrosine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / isopropyl alcohol; water
2: hydrogen / palladium on carbon / methanol / 1.33 h / 50 °C / 2250.23 Torr
3: hydrogen bromide / water / 4 h / 120 °C
View Scheme
3-(4-methoxyphenyl)-2-methyl-2-((1S)-1-phenyl-ethylamino)-propionamide hydrochloride
1299492-12-8

3-(4-methoxyphenyl)-2-methyl-2-((1S)-1-phenyl-ethylamino)-propionamide hydrochloride

L-methyltyrosine
672-87-7

L-methyltyrosine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2-methyl-propan-1-ol / Heating; Reflux
2: hydrogen / palladium on carbon / methanol / 1.33 h / 50 °C / 2250.23 Torr
3: hydrogen bromide / water / 4 h / 120 °C
View Scheme
(2S)-3-(4-methoxyphenyl)-2-methyl-2-((1S)-1-phenyl-ethylamino)-propionamide hydrochloride

(2S)-3-(4-methoxyphenyl)-2-methyl-2-((1S)-1-phenyl-ethylamino)-propionamide hydrochloride

L-methyltyrosine
672-87-7

L-methyltyrosine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen / palladium on carbon / methanol / 1.33 h / 50 °C / 2250.23 Torr
2: hydrogen bromide / water / 4 h / 120 °C
View Scheme
C22H26ClNO3
1299492-17-3

C22H26ClNO3

L-methyltyrosine
672-87-7

L-methyltyrosine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / isopropyl alcohol; water / 1 h / 20 °C
2: boron tribromide / dichloromethane / 1.5 h / 20 °C
View Scheme
2-amino-3-(4-hydroxy-phenyl)-2-methyl-propionic acid
658-48-0

2-amino-3-(4-hydroxy-phenyl)-2-methyl-propionic acid

A

L-methyltyrosine
672-87-7

L-methyltyrosine

B

α-methyl-D-tyrosine
672-86-6

α-methyl-D-tyrosine

Conditions
ConditionsYield
With Merck RP-18 WF254S plates coated with Nτ-n-decyl-L-spinacine and Cu acetate In ethanol; water Resolution of racemate;
N-(benzylidene)-O-methoxymethyl tyrosine tert-butyl ester

N-(benzylidene)-O-methoxymethyl tyrosine tert-butyl ester

methyl iodide
74-88-4

methyl iodide

L-methyltyrosine
672-87-7

L-methyltyrosine

Conditions
ConditionsYield
Stage #1: N-(benzylidene)-O-methoxymethyl tyrosine tert-butyl ester; methyl iodide With ((11bS)-(+)-4,4-dibutyl-4,5-dihydro-2,6-bis(3,4,5-triflourophenyl)-3H-dinaphth[2,1-c:1’,2’-e]azepinium bromide); cesium hydroxide In toluene at 0℃; for 0.5h; Inert atmosphere;
Stage #2: With hydrogenchloride In water; toluene at 60℃; for 0.5h; Inert atmosphere; stereoselective reaction;
n/a
(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

L-methyltyrosine
672-87-7

L-methyltyrosine

Fmoc-L-(α-Me)Tyr-OH
246539-83-3

Fmoc-L-(α-Me)Tyr-OH

Conditions
ConditionsYield
With sodium hydroxide In acetonitrile at 20℃; for 3h; Acylation;100%
methanol
67-56-1

methanol

L-methyltyrosine
672-87-7

L-methyltyrosine

(S)-2-amino-3-(4-hydroxy-phenyl)-2-methyl-propionic acid methyl ester hydrochloride

(S)-2-amino-3-(4-hydroxy-phenyl)-2-methyl-propionic acid methyl ester hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 0 - 20℃; Heating / reflux;96%
With thionyl chloride at 0 - 20℃;
With thionyl chloride at 20℃; for 24h; Inert atmosphere; Reflux;1.48 g
L-methyltyrosine
672-87-7

L-methyltyrosine

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

N-palmitoyl-α-methyl-L-tyrosine

N-palmitoyl-α-methyl-L-tyrosine

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 16h;89%
In N,N-dimethyl-formamide at 20℃; for 16h;89%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

L-methyltyrosine
672-87-7

L-methyltyrosine

Boc-(L)(α-Me)Tyr-OH
74825-83-5

Boc-(L)(α-Me)Tyr-OH

Conditions
ConditionsYield
Stage #1: L-methyltyrosine With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine In dichloromethane Inert atmosphere;
Stage #2: di-tert-butyl dicarbonate In dichloromethane Inert atmosphere;
Stage #3: With methanol for 0.5h; Inert atmosphere;
67%
With sodium hydroxide; sodium hydrogencarbonate In 1,4-dioxane at 20℃; pH=8 - 9;60%
With sodium hydroxide; tert-butyl alcohol35%
cis-dichloro(2,2′-bipyridine)ruthenium(II)chloride

cis-dichloro(2,2′-bipyridine)ruthenium(II)chloride

L-methyltyrosine
672-87-7

L-methyltyrosine

sodium perchlorate

sodium perchlorate

Ru(N2C10H8)2(NH2CCH3CH2C6H4OHCOO)(1+)*ClO4(1-)*2.5H2O=Ru(N2C10H8)2(NH2CCH3CH2C6H4OHCOO)ClO4*2.5H2O

Ru(N2C10H8)2(NH2CCH3CH2C6H4OHCOO)(1+)*ClO4(1-)*2.5H2O=Ru(N2C10H8)2(NH2CCH3CH2C6H4OHCOO)ClO4*2.5H2O

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water Ru-complex was refluxed in mixt. of H2O and EtOH, to this soln. was added ligand followed by aq. NaOH, mixt. was heated at 70°C for 30 min, cooled to room temp., filtered, aq. soln. of NaClO4 was added, mixt.was stored in the dark for 48 h; solid was collected at the pump, washed with ice-cold H2O, dried in vac. over silica gel at room temp.; elem. anal.;41%
cis-dichloridobis(1,10-phenanthroline)ruthenium(II)

cis-dichloridobis(1,10-phenanthroline)ruthenium(II)

L-methyltyrosine
672-87-7

L-methyltyrosine

sodium perchlorate

sodium perchlorate

Ru(N2C12H8)2(NH2CCH3CH2C6H4OHCOO)(1+)*ClO4(1-)=Ru(N2C12H8)2(NH2CCH3CH2C6H4OHCOO)ClO4

Ru(N2C12H8)2(NH2CCH3CH2C6H4OHCOO)(1+)*ClO4(1-)=Ru(N2C12H8)2(NH2CCH3CH2C6H4OHCOO)ClO4

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water Ru-complex was refluxed in mixt. of H2O and EtOH, to this soln. was added ligand followed by aq. NaOH, mixt. was heated at 70°C for 30 min, cooled to room temp., filtered, aq. soln. of NaClO4 was added, mixt.was stored in the dark for 48 h; solid was collected at the pump, washed with ice-cold H2O, dried in vac. over silica gel at room temp.; elem. anal.;39%
L-methyltyrosine
672-87-7

L-methyltyrosine

A

L-3-18F-α-methyltyrosine

L-3-18F-α-methyltyrosine

B

[18F]-3,5-difluoro-L-α-methyltyrosine

[18F]-3,5-difluoro-L-α-methyltyrosine

Conditions
ConditionsYield
With 18F-fluoride In formic acid at 4℃; Product distribution; Further Variations:; Solvents; Temperatures;A 13%
B 2%
With 18F-fluoride; hydrogen fluoride; boron trifluoride
L-methyltyrosine
672-87-7

L-methyltyrosine

3-iodo-α-methyl-L-tyrosine

3-iodo-α-methyl-L-tyrosine

Conditions
ConditionsYield
With ammonium hydroxide; iodine; potassium iodide
L-methyltyrosine
672-87-7

L-methyltyrosine

benzyl chloroformate
501-53-1

benzyl chloroformate

(S)-N2-<(benzyloxy)carbonyl>-2-methyltyrosine

(S)-N2-<(benzyloxy)carbonyl>-2-methyltyrosine

Conditions
ConditionsYield
With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine 1.) CHCl3, 70 deg C, 1 h; 2.) CHCl3, 70 deg C, 1 h; 3.) CHCl3, 80 deg C, 17 h; Yield given. Multistep reaction;
L-methyltyrosine
672-87-7

L-methyltyrosine

L-3-18F-α-methyltyrosine

L-3-18F-α-methyltyrosine

Conditions
ConditionsYield
With 18F-fluoride; hydrogen fluoride
methanol
67-56-1

methanol

L-methyltyrosine
672-87-7

L-methyltyrosine

α-methyl-para-tyrosine methyl ester
7423-78-1

α-methyl-para-tyrosine methyl ester

Conditions
ConditionsYield
With thionyl chloride Heating;
L-methyltyrosine
672-87-7

L-methyltyrosine

Boc-(L)(α-Me)Tyr-OMe
675106-56-6

Boc-(L)(α-Me)Tyr-OMe

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2 / Heating
2: aq. NaHCO3; NaOH / dioxane / 20 °C / pH 8 - 9
View Scheme
L-methyltyrosine
672-87-7

L-methyltyrosine

Boc-(L)(α-Me)Tyr(Tf)-OMe
675106-57-7

Boc-(L)(α-Me)Tyr(Tf)-OMe

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SOCl2 / Heating
2: aq. NaHCO3; NaOH / dioxane / 20 °C / pH 8 - 9
3: 80 percent / Et3N / CH2Cl2 / 3 h / 20 °C
View Scheme
L-methyltyrosine
672-87-7

L-methyltyrosine

Boc-(L)(α-Me)Phe(4-PO3Et2)-OMe
675106-58-8

Boc-(L)(α-Me)Phe(4-PO3Et2)-OMe

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: SOCl2 / Heating
2: aq. NaHCO3; NaOH / dioxane / 20 °C / pH 8 - 9
3: 80 percent / Et3N / CH2Cl2 / 3 h / 20 °C
4: 77 percent / Pd(PPh3)4; N-methylmorpholine / acetonitrile / Heating
View Scheme
L-methyltyrosine
672-87-7

L-methyltyrosine

Boc-(α-Me)Tyr-Asn-NH2
675106-63-5

Boc-(α-Me)Tyr-Asn-NH2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 percent / aq. NaHCO3; NaOH / dioxane / 20 °C / pH 8 - 9
2: 86 percent / DIEA; HOAt; HATU / dimethylformamide / 72 h / 20 °C
View Scheme
L-methyltyrosine
672-87-7

L-methyltyrosine

(L)(α-Me)Phe(4-PO3H2)-OH*HCl

(L)(α-Me)Phe(4-PO3H2)-OH*HCl

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: SOCl2 / Heating
2: aq. NaHCO3; NaOH / dioxane / 20 °C / pH 8 - 9
3: 80 percent / Et3N / CH2Cl2 / 3 h / 20 °C
4: 77 percent / Pd(PPh3)4; N-methylmorpholine / acetonitrile / Heating
5: 100 percent / aq. HCl / Heating
View Scheme
L-methyltyrosine
672-87-7

L-methyltyrosine

Boc-(α-Me)pTyr(Bzl2)-Asn-NH2
675106-65-7

Boc-(α-Me)pTyr(Bzl2)-Asn-NH2

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 60 percent / aq. NaHCO3; NaOH / dioxane / 20 °C / pH 8 - 9
2: 86 percent / DIEA; HOAt; HATU / dimethylformamide / 72 h / 20 °C
View Scheme
L-methyltyrosine
672-87-7

L-methyltyrosine

Boc-(α-Me)pTyr(MeSATE)2-Asn-NH2
675106-64-6

Boc-(α-Me)pTyr(MeSATE)2-Asn-NH2

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 60 percent / aq. NaHCO3; NaOH / dioxane / 20 °C / pH 8 - 9
2: 86 percent / DIEA; HOAt; HATU / dimethylformamide / 72 h / 20 °C
View Scheme
L-methyltyrosine
672-87-7

L-methyltyrosine

(α-Me)pTyr-Asn-NH2

(α-Me)pTyr-Asn-NH2

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 60 percent / aq. NaHCO3; NaOH / dioxane / 20 °C / pH 8 - 9
2: 86 percent / DIEA; HOAt; HATU / dimethylformamide / 72 h / 20 °C
3: 93 percent / CH2Cl2 / 3 h / 20 °C
View Scheme
L-methyltyrosine
672-87-7

L-methyltyrosine

(α-Me)pTyr(MeSATE)2-Asn-NH2

(α-Me)pTyr(MeSATE)2-Asn-NH2

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 60 percent / aq. NaHCO3; NaOH / dioxane / 20 °C / pH 8 - 9
2: 86 percent / DIEA; HOAt; HATU / dimethylformamide / 72 h / 20 °C
3: CH2Cl2 / 1 h / 0 °C
View Scheme

L-alpha-Methyltyrosine Chemical Properties

 Molecule structure of L-Tyrosine, a-methyl- (CAS NO.672-87-7):

IUPAC Name: (2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid
Molecular Weight: 195.21512 [g/mol]
Molecular Formula: C10H13NO3 
Index of Refraction: 1.599
Molar Refractivity: 52.01 cm3
Molar Volume: 152 cm3
Surface Tension: 60.6 dyne/cm
Density: 1.283 g/cm3 
Melting Point: 320-340 °C
Storage temp.: −20 °C
Flash Point: 185.9 °C
Enthalpy of Vaporization: 66.7 kJ/mol
Boiling Point: 383.7 °C at 760 mmHg
Vapour Pressure: 1.42E-06 mmHg at 25 °C
XLogP3-AA: -1.6
H-Bond Donor: 3
H-Bond Acceptor: 4
Rotatable Bond Count: 3
Tautomer Count: 2
Exact Mass: 195.089543
MonoIsotopic Mass: 195.089543
Topological Polar Surface Area: 83.6
Heavy Atom Count: 14
Canonical SMILES: CC(CC1=CC=C(C=C1)O)(C(=O)O)N
Isomeric SMILES: C[C@](CC1=CC=C(C=C1)O)(C(=O)O)N
InChI: InChI=1S/C10H13NO3/c1-10(11,9(13)14)6-7-2-4-8(12)5-3-7/h2-5,12H,6,11H2,1H3,(H,13,14)/t10-/m0/s1
InChIKey: NHTGHBARYWONDQ-JTQLQIEISA-N
EINECS: 211-599-5
Product Categories of L-Tyrosine, a-methyl- (CAS NO.672-87-7): Amino acids methyl、ethyl、t-butyl series;Amino Acids & Derivatives

L-alpha-Methyltyrosine Uses

 L-Tyrosine, a-methyl- (CAS NO.672-87-7) is a tyrosine hydroxylase inhibitor. It is also an antihypertensive in pheochromocytoma.

L-alpha-Methyltyrosine Safety Profile

Safety Statements: 22-24/25
S22:Do not breathe dust. 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3

L-alpha-Methyltyrosine Specification

 L-Tyrosine, a-methyl- (CAS NO.672-87-7) is also called Alpha-Methyltyrosine ; Metyrosine [USAN] ;
(-)-(S)-2-Amino-3-(4-hydroxyphenyl)-2-methylpropionsaeure ; (-)-alpha-Methyl-L-tyrosine (S)-alpha-Methyltyrosine ; Demser ; L-alpha-Methyltyrosine ; Metirosina ; Metirosina [INN-Spanish] ; Metirosinum ; Metirosinum [INN-Latin] ; Metyrosine ; L-Tyrosine, alpha-methyl-, (-)- ; Metirosine . It is white Solid. 

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