(S)-3-FMOC-AMINO-1-DIAZO-3-PHENYL-2-BUTANONE

Base Information

• Chemical Name: (S)-3-FMOC-AMINO-1-DIAZO-3-PHENYL-2-BUTANONE
• CAS No.: 172097-41-5
• Molecular Formula: C25H21N3O3
• Molecular Weight: 411.46
• Mol file: 172097-41-5.mol

Synonyms:Fmoc-(S)-Phe-CHN2;(S)-1-diazo-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-4-phenylbutan-2-one;((1S)-benzyl-3-diazo-2-oxo-propyl)carbamic acid 9H-fluoren-9-ylmethyl ester;Fmoc-L-phenylalanyl(diazo)methane;Fmoc-Phe-DAM;FMOC-L-PHE-CHN2;

Chemical Property of (S)-3-FMOC-AMINO-1-DIAZO-3-PHENYL-2-BUTANONE

Chemical Property:

• PSA: 92.79000
• LogP: 4.47806

Purity/Quality:

97% ^*data from raw suppliers

(S)-3-FMOC-AMINO-1-DIAZO-3-PHENYL-2-BUTANONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-3-FMOC-AMINO-1-DIAZO-3-PHENYL-2-BUTANONE

There total 7 articles about (S)-3-FMOC-AMINO-1-DIAZO-3-PHENYL-2-BUTANONE 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: 95.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + N-Fmoc L-Phe (35661-40-6) → (S)-1-diazo-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-phenylbutan-2-one (172097-41-5)

Guidance literature:

N-Fmoc L-Phe; With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -15 ℃; for 0.0833333h;

diazomethane; In tetrahydrofuran; diethyl ether; at -15 - 20 ℃; for 0.5h; Further stages.;

DOI:10.1021/ja029205t

Reference yield: 92.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 2S-flouren-9-ylmethoxycarbonylamino-3-phenylpropionyl chloride (103321-57-9) → (S)-1-diazo-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-phenylbutan-2-one (172097-41-5)

Guidance literature:

In dichloromethane; for 1h; Ambient temperature;

Reference yield:

N-Fmoc L-Phe (35661-40-6) → (S)-1-diazo-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-phenylbutan-2-one (172097-41-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NMM / tetrahydrofuran / 1 h / -25 °C

2: diethyl ether / 2 h / Ambient temperature

With 4-methyl-morpholine; In tetrahydrofuran; diethyl ether;

DOI:10.1016/S0040-4039(98)00675-3

upstream raw materials:

diazomethane

2S-flouren-9-ylmethoxycarbonylamino-3-phenylpropionyl chloride

N-Fmoc L-Phe

L-phenylalanine hydrochloride

Downstream raw materials:

H2N-Phe-(R)Pro-Asu-βhPhe-OH

Refernces

• 1、 Siciliano, Carlo,De Marco, Rosaria,Guidi, Ludovica Evelin,Spinella, Mariagiovanna,Liguori, Angelo. "A one-pot procedure for the preparation of N-9-fluorenylmethyloxycarbonyl- α-amino diazoketones from α-amino acids". . p. 10575 - 10582. Retrieved 2013/02/22.
• 2、 Kantharaju,Suresh Babu, Vommina V.. "Homologation of α-amino acids to β-amino acids: 9-Fluorenylmethyl chloroformate as a carboxyl group activating agent for the synthesis of Nα-protected aminoacyldiazomethanes". . p. 2152 - 2158. Retrieved 2007/10/03.