(-)-Indolmycin

Base Information

• Chemical Name: (-)-Indolmycin
• CAS No.: 21200-24-8
• Molecular Formula: C14H15N3O2
• Molecular Weight: 257.292
• Hs Code.: 2934999090
• Mol file: 21200-24-8.mol

Synonyms:(1R,5S)-(-)-5-(1-Indol-3-ylethyl)-2-(methylamino)-2-oxazolin-4-one;Indolemycin;2-Oxazolin-4-one,5-(1-indol-3-ylethyl)-2-(methylamino)-,(1R,5S)-(-);Indolmycin;4(5H)-Oxazolone,5-(1-(1H-indol-3-yl)ethyl)-2-(methylamino)-,(S-(R*,S*));PA 155 A;5-(1-Indol-3-ylethyl)-2-(methylamino)-2-oxazolin-4-one;Indomycin;(5S)-5-[(1R)-1-(1H-indol-3-yl)ethyl]-2-(methylamino)-1,3-oxazol-4-one;

Chemical Property of (-)-Indolmycin

Chemical Property:

• Vapor Pressure: 2.75E-07mmHg at 25°C
• Melting Point: 209-210°
• Boiling Point: 420.8°Cat760mmHg
• PKA: 16.65±0.30(Predicted)
• Flash Point: 208.3°C
• PSA: 69.97000
• Density: 1.36g/cm³
• LogP: 2.04810
• Solubility.: Soluble in ethanol;methanol;DMSO;dimethyl formamide

Purity/Quality:

97% ^*data from raw suppliers

Indolmycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: (-)-Indolmycin is an antibiotic derived from *Streptomyces albus* that exhibits antibacterial activity, particularly against Staphylococci. Its synthesis involves key intermediates like (+)-indolmycenic ester, achieved through a lipase-catalyzed kinetic resolution, which ensures high optical purity. The compound's absolute configuration was confirmed via NMR analysis of derived (+)-MTPA esters, validating its stereochemical integrity. This method demonstrates an efficient approach to producing (-)-indolmycin with potential therapeutic applications.

Technology Process of (-)-Indolmycin

There total 26 articles about (-)-Indolmycin 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: 99.0%

5-<1-(1H-indol-3-yl)ethyl>-2-(dimethylamino)-4(5H)-oxazolone (103871-34-7,103871-35-8,105311-51-1,105370-71-6,105370-72-7) + methylamine (74-89-5) → (+/-) indolmycin (13786-41-9,20864-78-2,20893-33-8,20906-43-8,21193-77-1,21200-23-7,21200-24-8,32475-90-4,32475-91-5)

Guidance literature:

at -6 ℃; for 1h;

DOI:10.1021/jo00375a030

Reference yield: 64.0%

methylamine (74-89-5) + (5S)-2-amino-5-[(1R)-1-(1H-indol-3-yl)ethyl]-2-oxazolin-4-one (20906-48-3) → (5S)-5-[(1R)-1-(1H-indol-3-yl)ethyl]-2-methylamino-2-oxazolin-4-one (21200-24-8)

Guidance literature:

In water; at 5 ℃; for 5h;

DOI:10.1248/cpb.49.1604

Reference yield: 60.0%

(5S)-2-amino-5-[(1R)-1-(1H-indol-3-yl)ethyl]-2-oxazolin-4-one (20906-48-3) → (5S)-5-[(1R)-1-(1H-indol-3-yl)ethyl]-2-methylamino-2-oxazolin-4-one (21200-24-8)

Guidance literature:

With methylamine;

upstream raw materials:

(2S,3R)-N-<2-hydroxy-3-(3-indolyl)-butanoyl>-N'-methylthiourea

methylamine

(5S)-2-amino-5-[(1R)-1-(1H-indol-3-yl)ethyl]-2-oxazolin-4-one

Indole-3-carboxaldehyde

Downstream raw materials:

(5S)-2-[N-(N-benzyloxycarbonyl-L-alanyl)-N-methyl]amino-5-[(1R)-1-(indol-3-yl)ethyl]-2-oxazolin-4-one

(5S)-5-[(1R)-1-(indol-3-yl)ethyl]-2-[N-(N-(4-methoxyphenyl)carbamoyl)-N-methyl]amino-2-oxazolin-4-one

(5S)-2-(N-benzyloxycarbonyl-N-methyl)amino-5[(1R)-1-(indol-3-yl)ethyl]-2-oxazolin-4-one

(5S)-2-[N-(2-benzyloxybenzoyl)-N-methyl]amino-5-[(1R)-1-(indol-3-yl)ethyl]-2-oxazolin-4-one

Refernces

Formal total synthesis of (-)-indolmycin

10.1248/cpb.38.323

The research focuses on the formal total synthesis of (-)-indolmycin, an antibiotic with antibacterial activity against Staphylococci, derived from an African strain of Streptomyces albus. The study aimed to prepare (+)-indolmycenic ester 4, a key intermediate for the synthesis of (-)-indolmycin, using a lipase-catalyzed kinetic resolution as a key step. The process involved the use of various chemicals, including epoxybutyrate derivatives, chlorohydrin, mesylate, and indole precursors. The researchers successfully synthesized (+)-indolmycenic ester 4 and formally accomplished the total synthesis of (-)-indolmycin, confirming its absolute configuration through the preparation of (+)-MTPA esters and NMR analysis. The study concluded that the lipase-catalyzed kinetic resolution was an effective method for achieving the synthesis with high optical purity.