D-Tryptophan, 6-methoxy-1-methyl-N-(phenylmethyl)-, ethyl ester

Base Information

• Chemical Name: D-Tryptophan, 6-methoxy-1-methyl-N-(phenylmethyl)-, ethyl ester
• CAS No.: 185418-93-3
• Molecular Formula: C22H26N2O3
• Molecular Weight: 366.46
• Mol file: 185418-93-3.mol

Synonyms:

Chemical Property of D-Tryptophan, 6-methoxy-1-methyl-N-(phenylmethyl)-, ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of D-Tryptophan, 6-methoxy-1-methyl-N-(phenylmethyl)-, ethyl ester

There total 6 articles about D-Tryptophan, 6-methoxy-1-methyl-N-(phenylmethyl)-, ethyl 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: 93.0%

benzaldehyde (100-52-7) + 6-methoxy-Na-methyl-D-tryptophan ethyl ester (185419-25-4) → Nα-benzyl-6-methoxy-1-methyl-D-tryptophane ethyl ester (185418-93-3)

Guidance literature:

benzaldehyde; 6-methoxy-N_a-methyl-D-tryptophan ethyl ester; In ethanol; at 20 ℃; for 5h;

With sodium tetrahydroborate; In ethanol; at -10 - -5 ℃; for 4h;

DOI:10.1021/jo040282b

Reference yield:

2-iodo-5-methoxyaniline (153898-63-6) → Nα-benzyl-6-methoxy-1-methyl-D-tryptophane ethyl ester (185418-93-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 77 percent / lithium chloride; sodium carbonate / palladium(II) acetate / dimethylformamide / 36 h / 100 °C

2.1: 95 percent / sodium hydride / dimethylformamide; various solvent(s) / 2 h / 0 °C

3.1: 93 percent / HCl / tetrahydrofuran; H₂O / 0 - 20 °C

4.1: ethanol / 5 h / 20 °C

4.2: 93 percent / NaBH₄ / ethanol / 4 h / -10 - -5 °C

With hydrogenchloride; sodium hydride; sodium carbonate; lithium chloride; palladium diacetate; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; 1.1: Larock heteroannulation;

DOI:10.1021/jo040282b

Reference yield:

(2S,5R)-3,6-diethoxy-2-isopropyl-5-[3-(triethylsilyl)prop-2-ynyl]-2,5-dihydropyrazine (355839-49-5) → Nα-benzyl-6-methoxy-1-methyl-D-tryptophane ethyl ester (185418-93-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 77 percent / lithium chloride; sodium carbonate / palladium(II) acetate / dimethylformamide / 36 h / 100 °C

2.1: 95 percent / sodium hydride / dimethylformamide; various solvent(s) / 2 h / 0 °C

3.1: 93 percent / HCl / tetrahydrofuran; H₂O / 0 - 20 °C

4.1: ethanol / 5 h / 20 °C

4.2: 93 percent / NaBH₄ / ethanol / 4 h / -10 - -5 °C

With hydrogenchloride; sodium hydride; sodium carbonate; lithium chloride; palladium diacetate; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; 1.1: Larock heteroannulation;

DOI:10.1021/jo040282b

upstream raw materials:

benzaldehyde

6-methoxy-N_a-methyl-D-tryptophan ethyl ester

2-iodo-5-methoxyaniline

(2S,5R)-3,6-diethoxy-2-isopropyl-5-[3-(triethylsilyl)prop-2-ynyl]-2,5-dihydropyrazine

Downstream raw materials:

(1S,3R)-2-Benzyl-1-(2-ethoxycarbonyl-ethyl)-7-methoxy-9-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid ethyl ester

trans-(1S,3R)-(-)-2-benzyl-3-ethoxycarbonyl-7-methoxy-1-methoxycarbonylethyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole

C₂₅H₂₆N₂O₄