beta-(isoxazolin-5-on-4-yl)alanine

Base Information

• Chemical Name: beta-(isoxazolin-5-on-4-yl)alanine
• CAS No.: 127607-88-9
• Molecular Formula: C6H8 N2 O4
• Molecular Weight: 172.1387
• Mol file: 127607-88-9.mol

Synonyms:4-Isoxazolepropanoicacid, a-amino-2,5-dihydro-5-oxo-, (S)-;Antibiotic TAN 950A; TAN 950A; b-(Isoxazolin-5-on-4-yl)-L-alanine

Chemical Property of beta-(isoxazolin-5-on-4-yl)alanine

Chemical Property:

• Vapor Pressure: 0.000881mmHg at 25°C
• Boiling Point: 304.3°Cat760mmHg
• Flash Point: 137.8°C
• PSA: 98.32000
• Density: 1.379g/cm³
• LogP: 0.01770

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of beta-(isoxazolin-5-on-4-yl)alanine

There total 7 articles about beta-(isoxazolin-5-on-4-yl)alanine 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:

dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate (59279-60-6,130622-05-8,861658-15-3) → TAN 950A (127607-88-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 31 percent / lithium diisopropylamide / tetrahydrofuran; hexane / -78 - -20 °C

2: 91 percent / NH₂OH*HCl / H₂O; dioxane / 1 h / Ambient temperature

3: 75 percent / 2N NaOH / methanol / 2 h / Ambient temperature

4: 87 percent / 2N NaOH / methanol / 2 h / Ambient temperature

5: trifluoroacetic acid / 30 h / Ambient temperature

With sodium hydroxide; hydroxylamine hydrochloride; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; water;

DOI:10.1016/S0040-4020(01)91004-X

Reference yield:

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one (108963-96-8) → TAN 950A (127607-88-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 46 percent / lithium bis-(trimethylsilyl)amide / tetrahydrofuran; hexane / -78 - -40 °C

2: 91 percent / NH₂OH*HCl / H₂O; dioxane / 1 h / Ambient temperature

3: 75 percent / 2N NaOH / methanol / 2 h / Ambient temperature

4: 87 percent / 2N NaOH / methanol / 2 h / Ambient temperature

5: trifluoroacetic acid / 30 h / Ambient temperature

With sodium hydroxide; hydroxylamine hydrochloride; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; water;

DOI:10.1016/S0040-4020(01)91004-X

Reference yield:

γ-formyl-N-Boc-L-pyroglutamic acid methyl ester (127706-22-3) → TAN 950A (127607-88-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / NH₂OH*HCl / H₂O; dioxane / 1 h / Ambient temperature

2: 75 percent / 2N NaOH / methanol / 2 h / Ambient temperature

3: 87 percent / 2N NaOH / methanol / 2 h / Ambient temperature

4: trifluoroacetic acid / 30 h / Ambient temperature

With sodium hydroxide; hydroxylamine hydrochloride; trifluoroacetic acid; In 1,4-dioxane; methanol; water;

DOI:10.1016/S0040-4020(01)91004-X

upstream raw materials:

N-tert-butoxycarbonyl-TAN-950 A

O-acetyl-L-serine

3-isoxazolin-5-one

dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate

Downstream raw materials:

(S)-2-(4-Nitro-benzylamino)-3-[2-(4-nitro-benzyl)-5-oxo-2,5-dihydro-isoxazol-4-yl]-propionic acid 4-nitro-benzyl ester

(S)-4-(Hydroxyimino-methyl)-5-oxo-pyrrolidine-2-carboxylic acid 4-nitro-benzyl ester

(S)-4-(Hydroxyimino-methyl)-5-oxo-pyrrolidine-2-carboxylic acid 4-nitro-benzyl ester

N-benzoyl TAN-950 A

Refernces

• 1、 Tsubotani, Shigetoshi,Funabashi, Yasunori,Takamoto, Masayuki,Hakoda, Seiji,Harada, Setsuo. "A NOVEL AMINO ACID ANTIBIOTIC TAN-950". . p. 8079 - 8090. Retrieved 2007/10/02.