Benzeneacetic acid, a-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-hydroxy-,(S)- (9CI)

Base Information

• Chemical Name: Benzeneacetic acid, a-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-hydroxy-,(S)- (9CI)
• CAS No.: 182883-41-6
• Molecular Formula: C23H19 N O5
• Molecular Weight: 389.408
• Mol file: 182883-41-6.mol

Synonyms:FMOC-L-NORTYR;(S)-[(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)]-(4-HYDROXY-PHENYL)-ACETIC ACID;Fmoc-L-4-Hydroxyphenylglycine

Chemical Property of Benzeneacetic acid, a-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-hydroxy-,(S)- (9CI)

Chemical Property:

• PSA: 95.86000
• LogP: 4.44750
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-(4-hydroxyphenyl)aceticacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzeneacetic acid, a-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-hydroxy-,(S)- (9CI)

There total 1 articles about Benzeneacetic acid, a-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-hydroxy-,(S)- (9CI) 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: 83.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (S)-hydroxyphenylglycine (32462-30-9) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-(4-hydroxyphenyl)acetic acid (182883-41-6)

Guidance literature:

(S)-hydroxyphenylglycine; With sodium carbonate; In water; acetonitrile; at 20 ℃; for 0.166667h;

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; In water; acetonitrile; at 20 ℃;

DOI:10.1016/j.bmc.2022.116631

Reference yield: 48.0%

(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-(4-hydroxyphenyl)acetic acid (182883-41-6) + phenylboronic acid (98-80-6) → Nα-Fmoc-(4-phenyloxy)-L-phenylglycine

Guidance literature:

With pyridine; copper diacetate; In dichloromethane; at 20 ℃; Molecular sieve;

DOI:10.1021/acs.jmedchem.0c02042

Reference yield: 30.0%

2-thiophenylcarboxylic acid (527-72-0) + (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-(4-hydroxyphenyl)acetic acid (182883-41-6) + Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) + Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine (187618-60-6) + benzyl alcohol (100-51-6,185532-71-2) → N-((S)-1-(((S)-6-amino-1-(((S)-2-amino-1-(4-(benzyloxy)phenyl)-2-oxoethyl)amino)-1-oxohexan-2-yl)amino)-5-guanidino-1-oxopentan-2-yl)thiophene-2-carboxamide

Guidance literature:

(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-(4-hydroxyphenyl)acetic acid; With 2,4,6-trimethyl-pyridine; N-[({[(1Z)-1-cyano-2-ethoxy-2-oxoethylidene]amino}oxy)-(morpholin-4-yl)methylidene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

With piperidine; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h;

2-thiophenylcarboxylic acid; Fmoc-Lys(tert-butoxycarbonyl); Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; benzyl alcohol; Further stages;

DOI:10.1016/j.bmc.2022.116631

upstream raw materials:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(S)-hydroxyphenylglycine

Refernces

• 1、 Kühl, Nikos,Leuthold, Mila M.,Behnam, Mira A. M.,Klein, Christian D.. "Beyond Basicity: Discovery of Nonbasic DENV-2 Protease Inhibitors with Potent Activity in Cell Culture". supporting information. p. 4567 - 4587. Retrieved 2021/05/06.