L-α-methyl-tryptophan methyl ester

Base Information

• Chemical Name: L-α-methyl-tryptophan methyl ester
• CAS No.: 142854-50-0
• Molecular Formula: C₁₃H₁₆N₂O₂
• Molecular Weight: 232.282
• Mol file: 142854-50-0.mol

Synonyms:L-α-methyl-tryptophan methyl ester

Chemical Property of L-α-methyl-tryptophan methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-α-methyl-tryptophan methyl ester

There total 8 articles about L-α-methyl-tryptophan methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

3-((S)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-propyl)-indole-1-carboxylic acid benzyl ester → L-α-methyl-tryptophan methyl ester (142854-50-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 3h; Yield given; Ambient temperature;

DOI:10.1002/(SICI)1099-1344(199712)39:12<1019::AID-JLCR43>3.0.CO;2-T

Reference yield:

(S)-N-benzyloxycarbonyl-L-tryptophan methyl ester (2717-76-2,130812-44-1,130812-46-3) → L-α-methyl-tryptophan methyl ester (142854-50-0)

Guidance literature:

Multi-step reaction with 5 steps

1: trifluoroacetic acid / 96 h / Ambient temperature

2: Na₂CO₃ / dioxane; H₂O

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

4: trifluoroacetic acid / 1.5 h / Ambient temperature

5: H₂ / 10percent Pd/C / ethanol / 3 h / Ambient temperature

With hydrogen; sodium carbonate; trifluoroacetic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In 1,4-dioxane; ethanol; water;

DOI:10.1002/(SICI)1099-1344(199712)39:12<1019::AID-JLCR43>3.0.CO;2-T

Reference yield:

(2S,3aR,8aR)-3,3a,8,8a-Tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (169687-64-3) → L-α-methyl-tryptophan methyl ester (142854-50-0)

Guidance literature:

Multi-step reaction with 4 steps

1: Na₂CO₃ / dioxane; H₂O

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

3: trifluoroacetic acid / 1.5 h / Ambient temperature

4: H₂ / 10percent Pd/C / ethanol / 3 h / Ambient temperature

With hydrogen; sodium carbonate; trifluoroacetic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In 1,4-dioxane; ethanol; water;

DOI:10.1002/(SICI)1099-1344(199712)39:12<1019::AID-JLCR43>3.0.CO;2-T

upstream raw materials:

methanol

(S)-α-methyltryptophan

(S)-N-benzyloxycarbonyl-L-tryptophan methyl ester

(2S,3aR,8aR)-3,3a,8,8a-Tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Downstream raw materials:

β-alanine, N-<α-methyl-N-<<(2-methylcyclohexyl)oxy>carbonyl>-L-tryptophyl>-D-3-(phenylmethyl)-, phenylmethyl ester, (1S-trans)

β-alanine, N-<α-methyl-N-<<(2-methylcyclohexyl)oxy>carbonyl>-L-tryptophyl>-D-3-(phenylmethyl)-, phenylmethyl ester, (1R-trans)

Refernces

• 1、 Ekhato, I. Victor,Huang, Yun. "Tetrahydro-pyrrolo-[2,3-b]indole-1,2,8-tricarboxylic acid ester in the enantiospecific preparation of α-methyltryptophan: Application in the preparation of carbon-14 labeled PD 145942 and PD 154075". . p. 1019 - 1038. Retrieved 2007/10/03.