Product Name

  • Name

    ALPHA-METHYL-L-TRYPTOPHAN

  • EINECS
  • CAS No. 16709-25-4
  • Article Data10
  • CAS DataBase
  • Density 1.314 g/cm3
  • Solubility
  • Melting Point 168-172 °C
  • Formula C12H14N2O2
  • Boiling Point 444 °C at 760 mmHg
  • Molecular Weight 218.255
  • Flash Point 222.3 °C
  • Transport Information
  • Appearance Colourless solid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 16709-25-4 (ALPHA-METHYL-L-TRYPTOPHAN)
  • Hazard Symbols
  • Synonyms Tryptophan,α-methyl-, L- (8CI);(-)-α-Methyltryptophan;L-α-Methyltryptophan;α-Methyl-(S)-tryptophan;α-Methyl-L-tryptophan;
  • PSA 79.11000
  • LogP 2.13100

Synthetic route

methyl 2-(indol-3-ylmethyl)-2-aminopropionate
114524-80-0

methyl 2-(indol-3-ylmethyl)-2-aminopropionate

A

α-methyl-DL-tryptophan
56452-52-9

α-methyl-DL-tryptophan

B

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

C

α-methyl-(R)-tryptophan methyl ester
96551-27-8

α-methyl-(R)-tryptophan methyl ester

Conditions
ConditionsYield
With α-chymotrypsin In water at 37℃; for 40h; pH=5.0;A 4%
B n/a
C 88%
With α-chymotrypsin In water at 37℃; for 40h; pH=5.0;A 4%
B n/a
C n/a
...Expand
methyl 2-(indol-3-ylmethyl)-2-aminopropionate
114524-80-0

methyl 2-(indol-3-ylmethyl)-2-aminopropionate

A

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

B

α-methyl-(R)-tryptophan methyl ester
96551-27-8

α-methyl-(R)-tryptophan methyl ester

Conditions
ConditionsYield
With α-chymotrypsin In water at 37℃; for 40h; Product distribution; also other α-methyl-amino acid esters investigated;A n/a
B 88%
(S)-N2-benzoyl-2-methyltryptophan-methylester
116139-87-8

(S)-N2-benzoyl-2-methyltryptophan-methylester

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

Conditions
ConditionsYield
With hydrogenchloride In methanol Heating;87%
tert-butyl 3-{[(3S,5aR,6aS,7aS)-2,3,5,5a,6,6a,7,7a-octahydro-3,6,6,7a-tetramethyl-2-oxobicyclo[4.1.0]hept-1(6)eno[3,4-b][1,4]oxazin-3-yl]methyl}-1H-indole-1-carboxylate
1266681-04-2

tert-butyl 3-{[(3S,5aR,6aS,7aS)-2,3,5,5a,6,6a,7,7a-octahydro-3,6,6,7a-tetramethyl-2-oxobicyclo[4.1.0]hept-1(6)eno[3,4-b][1,4]oxazin-3-yl]methyl}-1H-indole-1-carboxylate

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

Conditions
ConditionsYield
Stage #1: tert-butyl 3-{[(3S,5aR,6aS,7aS)-2,3,5,5a,6,6a,7,7a-octahydro-3,6,6,7a-tetramethyl-2-oxobicyclo[4.1.0]hept-1(6)eno[3,4-b][1,4]oxazin-3-yl]methyl}-1H-indole-1-carboxylate With cesium hydroxide; water In ethanol at 70℃; for 4h;
Stage #2: With hydrogenchloride In water		86%
tert-butyl [3-(3S,6R)-N-1-(tert-butoxycarbonyl)-6-isopropyl-3-methyl-2-oxo-5-phenyl-1,2,3,6-tetrahydropyrazinylmethyl]-1H-1-indolecarboxylate

tert-butyl [3-(3S,6R)-N-1-(tert-butoxycarbonyl)-6-isopropyl-3-methyl-2-oxo-5-phenyl-1,2,3,6-tetrahydropyrazinylmethyl]-1H-1-indolecarboxylate

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

Conditions
ConditionsYield
With hydrogenchloride at 150℃; for 72h; Hydrolysis;40%
2-Amino-3-(1H-indol-3-yl)-2-methyl-propionic acid butyl ester
141784-94-3

2-Amino-3-(1H-indol-3-yl)-2-methyl-propionic acid butyl ester

A

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

B

(R)-2-Amino-3-(1H-indol-3-yl)-2-methyl-propionic acid butyl ester
141784-97-6

(R)-2-Amino-3-(1H-indol-3-yl)-2-methyl-propionic acid butyl ester

C

(S)-2-Amino-3-(1H-indol-3-yl)-2-methyl-propionic acid butyl ester
141784-94-3, 141784-97-6

(S)-2-Amino-3-(1H-indol-3-yl)-2-methyl-propionic acid butyl ester

Conditions
ConditionsYield
In various solvent(s) Ambient temperature; Candida lipolythica lipase (active component: Candida lypolythica esterase); Yield given. Yields of byproduct given;
In various solvent(s) Ambient temperature; Candida lipolythica lipase (active component: Candida lypolythica esterase); Yield given. Yields of byproduct given. Title compound not separated from byproducts;
...Expand
2-(2-Chloro-acetylamino)-3-(1H-indol-3-yl)-2-methyl-propionic acid
121704-33-4

2-(2-Chloro-acetylamino)-3-(1H-indol-3-yl)-2-methyl-propionic acid

A

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

B

(R)-2-(2-Chloro-acetylamino)-3-(1H-indol-3-yl)-2-methyl-propionic acid
121704-33-4

(R)-2-(2-Chloro-acetylamino)-3-(1H-indol-3-yl)-2-methyl-propionic acid

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;
(R)-Nα-(Methoxycarbonyl)-α-methyltryptophan methyl ester

(R)-Nα-(Methoxycarbonyl)-α-methyltryptophan methyl ester

A

α-methyl-DL-tryptophan
56452-52-9

α-methyl-DL-tryptophan

B

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

Conditions
ConditionsYield
With hydrogenchloride for 16h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
3-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-propyl)-indole-1-carboxylic acid benzyl ester

3-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-propyl)-indole-1-carboxylic acid benzyl ester

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol for 3h; Ambient temperature; Yield given;
DL-α-methyltryptophan
153-91-3

DL-α-methyltryptophan

A

α-methyl-DL-tryptophan
56452-52-9

α-methyl-DL-tryptophan

B

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

Conditions
ConditionsYield
resolution of racemate via chiral HPLC;
With Merck RP-18 WF254S plates coated with Nτ-n-decyl-L-spinacine and Cu acetate In water; acetonitrile Resolution of racemate;
(S)-benzyl 2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanoate
69876-37-5

(S)-benzyl 2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanoate

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: CF3COOH / 96 h / Ambient temperature
2: Na2CO3 / dioxane; H2O / 0 °C
3: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 1 h, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 2 h
4: trifluoroacetic acid / 1.5 h / Ambient temperature
5: H2 / 10percent Pd/C / ethanol / 3 h / Ambient temperature
View Scheme
dibenzyl (2S,3aR,8aR)-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indol-1,2 (2H)-dicarboxylate

dibenzyl (2S,3aR,8aR)-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indol-1,2 (2H)-dicarboxylate

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Na2CO3 / dioxane; H2O / 0 °C
2: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 1 h, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 2 h
3: trifluoroacetic acid / 1.5 h / Ambient temperature
4: H2 / 10percent Pd/C / ethanol / 3 h / Ambient temperature
View Scheme
(2S,3aR,8aS)-2,3,3a,8a-Tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid tribenzyl ester
200716-93-4

(2S,3aR,8aS)-2,3,3a,8a-Tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid tribenzyl ester

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 1 h, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 2 h
2: trifluoroacetic acid / 1.5 h / Ambient temperature
3: H2 / 10percent Pd/C / ethanol / 3 h / Ambient temperature
View Scheme
(2S,3aR,8aR)-2-Methyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid tribenzyl ester
200716-94-5

(2S,3aR,8aR)-2-Methyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid tribenzyl ester

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trifluoroacetic acid / 1.5 h / Ambient temperature
2: H2 / 10percent Pd/C / ethanol / 3 h / Ambient temperature
View Scheme
N-carbobenzyloxy-L-tryptophane
7432-21-5

N-carbobenzyloxy-L-tryptophane

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: Cs2CO3 / dimethylformamide
2: CF3COOH / 96 h / Ambient temperature
3: Na2CO3 / dioxane; H2O / 0 °C
4: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 1 h, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 2 h
5: trifluoroacetic acid / 1.5 h / Ambient temperature
6: H2 / 10percent Pd/C / ethanol / 3 h / Ambient temperature
View Scheme
(2R,4R)-2-(tert-Butyl)-3-(ethoxycarbonyl)-4-(indol-3-yl-methyl)-4-methyl-1,3-oxazolidin-5-one
170458-97-6

(2R,4R)-2-(tert-Butyl)-3-(ethoxycarbonyl)-4-(indol-3-yl-methyl)-4-methyl-1,3-oxazolidin-5-one

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95.7 percent / LiOH*H2O / 6 h / 40 °C
2: aq. 6 N HCl / 16 h / Heating
View Scheme
(4R)-2-(tert-Butyl)-3-(ethoxycarbonyl)-4-(indol-3-yl-methyl)-1,3-oxa4olidin-5-one

(4R)-2-(tert-Butyl)-3-(ethoxycarbonyl)-4-(indol-3-yl-methyl)-1,3-oxa4olidin-5-one

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 78.9 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 0.5 h, 2.) -78 deg C, 2 h
2: 95.7 percent / LiOH*H2O / 6 h / 40 °C
3: aq. 6 N HCl / 16 h / Heating
View Scheme
1-(t-butyloxycarbonyl)-3-(bromomethyl)indole
96551-21-2

1-(t-butyloxycarbonyl)-3-(bromomethyl)indole

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) HMPT, LDA / 1.) THF, -78 deg C, 40 min, 2.) THF, -78 deg C, 36 h
2: 59 percent / 1N MeONa / methanol / 24 h / Ambient temperature
3: 87 percent / 6N HCl / methanol / Heating
View Scheme
(2R,5S)-3-benzoyl-2-(tert-butyl)-4-(<1-(tert-butyloxycarbonyl)-1H-indol-3-yl>methyl)-4-methyl-5-oxazolidinon
116139-85-6

(2R,5S)-3-benzoyl-2-(tert-butyl)-4-(<1-(tert-butyloxycarbonyl)-1H-indol-3-yl>methyl)-4-methyl-5-oxazolidinon

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 59 percent / 1N MeONa / methanol / 24 h / Ambient temperature
2: 87 percent / 6N HCl / methanol / Heating
View Scheme
methanol
67-56-1

methanol

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

L-α-methyl-tryptophan methyl ester
142854-50-0

L-α-methyl-tryptophan methyl ester

Conditions
ConditionsYield
With thionyl chloride Yield given. Multistep reaction;
2-adamantyloxychloroformate

2-adamantyloxychloroformate

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

2-[(Adamantan-2-yl-oxy)-carbonyl]-amino-3-(1H-indol-3-yl)-2RS-methyl-propionic acid
130406-42-7

2-[(Adamantan-2-yl-oxy)-carbonyl]-amino-3-(1H-indol-3-yl)-2RS-methyl-propionic acid

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane
1-aminomethyl-1-(5-hydroxypyridin-2-yl)cyclohexane hydrobromide

1-aminomethyl-1-(5-hydroxypyridin-2-yl)cyclohexane hydrobromide

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

(S)-2-amino-3-(1H-indol-3-yl)-N-[1-(5-hydroxypyridin-2-yl)cyclohexylmethyl]-2-methylpropionamide

(S)-2-amino-3-(1H-indol-3-yl)-N-[1-(5-hydroxypyridin-2-yl)cyclohexylmethyl]-2-methylpropionamide

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In tetrahydrofuran at 20℃;
1-aminomethyl-1-(4-(2-fluoroethoxy)phenyl)cycloexane hydrochloride

1-aminomethyl-1-(4-(2-fluoroethoxy)phenyl)cycloexane hydrochloride

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

(S)-2-amino-3-(1H-indol-3-yl)-N-[1-(4-(2-fluoroethoxy)phenyl)cyclohexylmethyl]-2-methylpropionamide

(S)-2-amino-3-(1H-indol-3-yl)-N-[1-(4-(2-fluoroethoxy)phenyl)cyclohexylmethyl]-2-methylpropionamide

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In tetrahydrofuran at 20℃;
1-aminomethyl-1-(2-fluoropyridin-4-yl)cycloexane

1-aminomethyl-1-(2-fluoropyridin-4-yl)cycloexane

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

(S)-2-amino-3-(1H-indol-3-yl)-N-[1-(2-fluoropyridin-5-yl)-cyclohexylmethyl]-2-methylpropionamide

(S)-2-amino-3-(1H-indol-3-yl)-N-[1-(2-fluoropyridin-5-yl)-cyclohexylmethyl]-2-methylpropionamide

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In tetrahydrofuran at 20℃;
1-aminomethyl-1-(2-fluoropyridin-5-yl)cycloexane

1-aminomethyl-1-(2-fluoropyridin-5-yl)cycloexane

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

(S)-2-amino-3-(1H-indol-3-yl)-N-[1-(2-fluoropyridin-5-yl)-cyclohexylmethyl]-2-methylpropionamide

(S)-2-amino-3-(1H-indol-3-yl)-N-[1-(2-fluoropyridin-5-yl)-cyclohexylmethyl]-2-methylpropionamide

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In tetrahydrofuran at 20℃;
1-aminomethyl-1-(2-fluoropyridin-5-yl)cycloexane

1-aminomethyl-1-(2-fluoropyridin-5-yl)cycloexane

(S)-α-methyltryptophan
16709-25-4

(S)-α-methyltryptophan

(S)-3-(1H-indol-3-yl)-N-[1-(2-fluoropyrid-5-yl)cyclohexylmethyl]-2-methyl-2-[3-(4-nitrophenyl)ureido]propionamide

(S)-3-(1H-indol-3-yl)-N-[1-(2-fluoropyrid-5-yl)cyclohexylmethyl]-2-methyl-2-[3-(4-nitrophenyl)ureido]propionamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / tetrahydrofuran / 20 °C
2: tetrahydrofuran / 24 h / 20 °C
View Scheme

L-Tryptophan,α-methyl- Specification

The CAS register number of L-Tryptophan,α-methyl- is 16709-25-4. It also can be called as L-α-Methyltryptophan and the systematic name about this chemical is α-methyl-L-tryptophan. The molecular formula about this chemical is C12H14N2O2 and the molecular weight is 218.25. It belongs to the following product categories which include Amino Acids 13C, 2H, 15N; Amino Acids & Derivatives; Chiral Reagents; Heterocycles; Indole Derivatives and so on. The usage of this chemical is a therapeutic and carrier molecule.

Physical properties about L-Tryptophan,α-methyl- are: (1)ACD/LogP: 1.39; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 4; (7)#H bond donors: 4; (8)#Freely Rotating Bonds: 4; (9)Polar Surface Area: 34.47 Å2; (10)Index of Refraction: 1.675; (11)Molar Refractivity: 62.4 cm3; (12)Molar Volume: 166 cm3; (13)Polarizability: 24.74x10-24cm3; (14)Surface Tension: 65.7 dyne/cm; (15)Density: 1.314 g/cm3; (16)Flash Point: 222.3 °C; (17)Enthalpy of Vaporization: 73.96 kJ/mol; (18)Boiling Point: 444 °C at 760 mmHg; (19)Vapour Pressure: 1.15E-08 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)[C@](N)(C)Cc2c1ccccc1nc2
(2)InChI: InChI=1/C12H14N2O2/c1-12(13,11(15)16)6-8-7-14-10-5-3-2-4-9(8)10/h2-5,7,14H,6,13H2,1H3,(H,15,16)/t12-/m0/s1
(3)InChIKey: ZTTWHZHBPDYSQB-LBPRGKRZBW
(4)Std. InChI: InChI=1S/C12H14N2O2/c1-12(13,11(15)16)6-8-7-14-10-5-3-2-4-9(8)10/h2-5,7,14H,6,13H2,1H3,(H,15,16)/t12-/m0/s1
(5)Std. InChIKey: ZTTWHZHBPDYSQB-LBPRGKRZSA-N

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