5-Isoxazoleacetic acid, alpha-amino-3-chloro-4,5-dihydro-

Base Information

• Chemical Name: 5-Isoxazoleacetic acid, alpha-amino-3-chloro-4,5-dihydro-
• CAS No.: 52583-41-2
• Molecular Formula: C5H7 Cl N2 O3
• Molecular Weight: 178.575
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID80860588
• Nikkaji Number: J379.780E
• Wikidata: Q26841004
• ChEMBL ID: CHEMBL1337040
• Mol file: 52583-41-2.mol

Synonyms:acivicin;alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid;alpha-S,5S-alpha-amino-3-chloro-2-isoxazoline-5-acetic acid;AT 125;AT-125;L-(alphaS,5S)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid;NSC 163501;U 42,126;U-42,126

Chemical Property of 5-Isoxazoleacetic acid, alpha-amino-3-chloro-4,5-dihydro-

Chemical Property:

• Boiling Point: 341.6°Cat760mmHg
• Flash Point: 160.4°C
• PSA: 84.91000
• Density: 1.85g/cm³
• LogP: -0.12460
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 178.0145198
• Heavy Atom Count: 11
• Complexity: 206

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(ON=C1Cl)C(C(=O)O)N

Technology Process of 5-Isoxazoleacetic acid, alpha-amino-3-chloro-4,5-dihydro-

There total 13 articles about 5-Isoxazoleacetic acid, alpha-amino-3-chloro-4,5-dihydro- 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: 66.0%

→ acivicin (52583-41-2) + barium (7440-39-3)

Guidance literature:

Reference yield: 65.0%

erythro-DL-N-benzyloxycarbonyl-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid (76843-83-9,104754-65-6) → erythro-DL-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid <(+/-)-AT-125> (42228-92-2,52583-41-2,76898-56-1,80184-13-0,104832-77-1)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In benzene; Heating;

DOI:10.1021/ja00394a039

Reference yield:

erythro-DL-N-benzyloxycarbonyl-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid o-nitrobenzyl ester (76843-81-7,76879-01-1) → erythro-DL-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid <(+/-)-AT-125> (42228-92-2,52583-41-2,76898-56-1,80184-13-0,104832-77-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / Al-Hg / diethyl ether

2: 65 percent / (COCl)2, DMF / benzene / Heating

With oxalyl dichloride; aluminium amalgam; N,N-dimethyl-formamide; In diethyl ether; benzene;

DOI:10.1021/ja00394a039

upstream raw materials:

(R)-((R)-3-chloro-4,5-dihydro-isoxazol-5-yl)-phthalimido-acetic acid

2,2,2-Trichloro-N-[(R)-1-((S)-3-chloro-4,5-dihydro-isoxazol-5-yl)-2-hydroxy-ethyl]-acetamide

erythro-DL-N-benzyloxycarbonyl-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid

(S)-Amino-((R)-3-chloro-4,5-dihydro-isoxazol-5-yl)-acetic acid; hydrochloride

Refernces

• 1、 Baldwin, Jack E.,Cha, Jin K.,Kruse, Lawrence I.. "TOTAL SYNTHESIS OF ANTITUMOR AGENT AT-125, (αS,5S)-α-AMINO-3-CHLORO-4,5-DIHYDRO-5-ISOXAZOLEACETIC ACID". . p. 5241 - 5260. Retrieved 2007/10/02.
• 2、 Baldwin, Jack E.,Kruse, Lawrence I.,Cha, Jin-Kun. "Total Synthesis of Antitumor Agent AT-125, (αS,5S)-α-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetic Acid". . p. 942 - 943. Retrieved 2007/10/02.