5-HYDROXY-ALPHA-METHYL-L-TRYPTOPHAN

Base Information

• Chemical Name: 5-HYDROXY-ALPHA-METHYL-L-TRYPTOPHAN
• CAS No.: 150852-19-0
• Molecular Formula: C₁₂H₁₄N₂O₃
• Molecular Weight: 234.255
• Mol file: 150852-19-0.mol

Synonyms:L-TRYPTOPHAN, 5-HYDROXY-ALPHA-METHYL-;5-HYDROXY-ALPHA-METHYL-L-TRYPTOPHAN;5-OH-ALPHA-METHYL-L-TRYPTOPHAN

Chemical Property of 5-HYDROXY-ALPHA-METHYL-L-TRYPTOPHAN

Chemical Property:

• PSA: 99.34000
• LogP: 1.91830

Purity/Quality:

99% ^*data from raw suppliers

5-HYDROXY-ALPHA-METHYL-L-TRYPTOPHAN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-HYDROXY-ALPHA-METHYL-L-TRYPTOPHAN

There total 7 articles about 5-HYDROXY-ALPHA-METHYL-L-TRYPTOPHAN 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:

(S)-3-(5-Hydroxy-1H-indol-3-yl)-2-methoxycarbonylamino-2-methyl-propionic acid methyl ester (150804-47-0) → 5-hydroxy-α-methyltryptophan (150852-19-0)

Guidance literature:

With potassium hydroxide; for 67h; Heating;

DOI:10.3987/COM-92-6313

Reference yield:

methyl (S)-3-(5-hydroxy-1H-indol-3-yl)-2-((methoxycarbonyl)amino)propanoate → 5-hydroxy-α-methyltryptophan (150852-19-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 85percent aq. phosphoric acid / Ambient temperature

2: 65 percent / pyridine

3: 1.) lithium diisopropylamide / 1.) THF, -78 deg C

4: 95 percent / trifluoroacetic acid / Ambient temperature

5: Na, HN₃ / 63 h

6: 5M aq. KOH / 67 h / Heating

With pyridine; potassium hydroxide; tris-(2-chloro-ethyl)-amine; phosphoric acid; sodium; trifluoroacetic acid; lithium diisopropyl amide;

DOI:10.3987/COM-92-6313

Reference yield:

(2S,3aR,8aR)-5-Hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid dimethyl ester (150852-18-9) → 5-hydroxy-α-methyltryptophan (150852-19-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 65 percent / pyridine

2: 1.) lithium diisopropylamide / 1.) THF, -78 deg C

3: 95 percent / trifluoroacetic acid / Ambient temperature

4: Na, HN₃ / 63 h

5: 5M aq. KOH / 67 h / Heating

With pyridine; potassium hydroxide; tris-(2-chloro-ethyl)-amine; sodium; trifluoroacetic acid; lithium diisopropyl amide;

DOI:10.3987/COM-92-6313

upstream raw materials:

(S)-3-(5-Hydroxy-1H-indol-3-yl)-2-methoxycarbonylamino-2-methyl-propionic acid methyl ester

(2S,3aR,8aR)-5-Hydroxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid dimethyl ester

(S)-3-(1-Benzenesulfonyl-5-benzenesulfonyloxy-1H-indol-3-yl)-2-methoxycarbonylamino-2-methyl-propionic acid methyl ester

(2S,3aR,8aS)-8-Benzenesulfonyl-5-benzenesulfonyloxy-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid dimethyl ester

Refernces