Tryptophan, N-benzoyl-, methyl ester (7CI)

Base Information

• Chemical Name: Tryptophan, N-benzoyl-, methyl ester (7CI)
• CAS No.: 2717-75-1
• Molecular Formula: C19H18N2O3
• Molecular Weight: 322.364
• Mol file: 2717-75-1.mol

Synonyms:Tryptophan, N-benzoyl-, methyl ester (7CI)

Chemical Property of Tryptophan, N-benzoyl-, methyl ester (7CI)

Chemical Property:

• Vapor Pressure: 1.4E-14mmHg at 25°C
• Boiling Point: 604.8°Cat760mmHg
• PKA: 13.12±0.46(Predicted)
• Flash Point: 319.6°C
• PSA: 74.68000
• Density: 1.257g/cm³
• LogP: 3.25680

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Tryptophan, N-benzoyl-, methyl ester (7CI)

There total 17 articles about Tryptophan, N-benzoyl-, methyl ester (7CI) 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: 98.0%

(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) + benzoyl chloride (98-88-4) → N-benzoyl-L-tryptophan methyl ester (2717-75-1)

Guidance literature:

With potassium carbonate; In water; ethyl acetate; for 1h; Ambient temperature;

Reference yield: 93.0%

methanol (67-56-1) + 4-(1H-indol-3-ylmethyl)-2-phenyl-4H-oxazolin-5-one (101693-51-0,97485-17-1) → N-benzoyl-L-tryptophan methyl ester (2717-75-1)

Guidance literature:

With Boc-Dmaa-D-pro-Aic-Ser(Bn)-NMe₂; In toluene; at 4 ℃; for 23h; enantioselective reaction;

DOI:10.1021/jo402828f

Reference yield: 75.0%

benzoic acid (65-85-0,8013-63-6) + L-tryptophan methyl ester (4299-70-1) → N-benzoyl-L-tryptophan methyl ester (2717-75-1)

Guidance literature:

With tetrakis(dimethylamido)diborane; In toluene; for 7h; Reflux;

DOI:10.1021/acs.orglett.8b01480

upstream raw materials:

indole

(S)-1-Benzoyl-aziridine-2-carboxylic acid methyl ester

(S)-tryptophan methyl ester hydrochloride

benzoyl chloride

Downstream raw materials:

3-(2-phenyl-4-carbomethoxy-5-oxazolyl)indole

1-benzoyl-1,2,3,8-tetrahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester

N-benzoyl-L-tryptophane

C₂₈H₃₅N₃O₄

Refernces

• 1、 Movahed, Farzaneh Soleymani,Sawant, Dinesh N.,Bagal, Dattatraya B.,Saito, Susumu. "Tris(o-phenylenedioxy)cyclotriphosphazene as a Promoter for the Formation of Amide Bonds between Aromatic Acids and Amines". . p. 3253 - 3262. Retrieved 2020/11/02.
• 2、 Sawant, Dinesh N.,Bagal, Dattatraya B.,Ogawa, Saeko,Selvam, Kaliyamoorthy,Saito, Susumu. "Diboron-Catalyzed Dehydrative Amidation of Aromatic Carboxylic Acids with Amines". supporting information. p. 4397 - 4400. Retrieved 2018/08/09.