(S)-(2-acetoxy)-1-((1H-indol-3-ylmethyl)ethyl)carbamic acid, phenylmethyl ester

Base Information

• Chemical Name: (S)-(2-acetoxy)-1-((1H-indol-3-ylmethyl)ethyl)carbamic acid, phenylmethyl ester
• CAS No.: 110815-27-5
• Molecular Formula: C₂₁H₂₂N₂O₄
• Molecular Weight: 366.417

Synonyms:(S)-(2-acetoxy)-1-((1H-indol-3-ylmethyl)ethyl)carbamic acid, phenylmethyl ester

Chemical Property of (S)-(2-acetoxy)-1-((1H-indol-3-ylmethyl)ethyl)carbamic acid, phenylmethyl ester

Chemical Property:

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Technology Process of (S)-(2-acetoxy)-1-((1H-indol-3-ylmethyl)ethyl)carbamic acid, phenylmethyl ester

There total 5 articles about (S)-(2-acetoxy)-1-((1H-indol-3-ylmethyl)ethyl)carbamic acid, phenylmethyl 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:

benzyl (S)-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate (61535-47-5,58889-48-8) + acetyl chloride (75-36-5) → (S)-(2-acetoxy)-1-((1H-indol-3-ylmethyl)ethyl)carbamic acid, phenylmethyl ester (110815-27-5)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 0.25h; Yield given;

DOI:10.1016/S0040-4020(01)87853-4

Reference yield:

(S)-tryptophan methyl ester hydrochloride (7524-52-9,26988-71-6,5619-09-0,14907-27-8,41222-70-2,67557-19-1,109492-62-8) → (S)-(2-acetoxy)-1-((1H-indol-3-ylmethyl)ethyl)carbamic acid, phenylmethyl ester (110815-27-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1 N NaOH / dioxane / 0.33 h

2: LiBH₄ / tetrahydrofuran / 1.) room temperature, 1 h, 2.) reflux, 1 h

3: pyridine / CH₂Cl₂ / 0.25 h / 0 °C

With pyridine; sodium hydroxide; lithium borohydride; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1016/S0040-4020(01)87853-4

Reference yield:

(S)-N-benzyloxycarbonyl-L-tryptophan methyl ester (2717-76-2,130812-44-1,130812-46-3) → (S)-(2-acetoxy)-1-((1H-indol-3-ylmethyl)ethyl)carbamic acid, phenylmethyl ester (110815-27-5)

Guidance literature:

Multi-step reaction with 2 steps

1: LiBH₄ / tetrahydrofuran / 1.) room temperature, 1 h, 2.) reflux, 1 h

2: pyridine / CH₂Cl₂ / 0.25 h / 0 °C

With pyridine; lithium borohydride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(01)87853-4

upstream raw materials:

acetic anhydride

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

benzyl (S)-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate

acetyl chloride

Downstream raw materials:

(R)-(1-((acetoxy)methyl)-2-(1H-indol-3-yl)-2-oxoethyl)carbamic acid phenylmethyl ester

(S,S)-(2-(4-((1-(((phenylmethyl)oxy)carbonyl)-2-methylpropyl)amino)-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester

(+)-Epi-indolactam-V

2-[3-((S)-2-Benzyloxycarbonylamino-3-hydroxy-propyl)-1H-indol-4-ylamino]-3-methyl-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester

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