N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-methionine

Base Information

• Chemical Name: N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-methionine
• CAS No.: 144701-23-5
• Molecular Formula: C20H21NO4S
• Molecular Weight: 371.457
• European Community (EC) Number: 276-258-5
• NSC Number: 334292
• DSSTox Substance ID: DTXSID50275948,DTXSID201315844
• Mol file: 144701-23-5.mol

Synonyms:Fmoc-DL-methionine;Fmoc-D-methionine;144701-23-5;2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylsulfanylbutanoic acid;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-methionine;112833-40-6;2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylsulfanyl-butanoic acid;N-Fmoc-D-methionine;2-({[(9H-FLUOREN-9-YL)METHOXY]CARBONYL}AMINO)-4-(METHYLSULFANYL)BUTANOIC ACID;L-Methionine-13C5,15N, N-Fmoc, N-(9-Fluorenylmethoxycarbonyl)-L-methionine-13C5,15N;EINECS 276-258-5;MFCD00037134;MFCD00062958;2-[[9H-fluoren-9-ylmethoxy(oxo)methyl]amino]-4-(methylthio)butanoic acid;DL-Fmoc-Methionine;NSC334292;N-((9H-Fluoren-9-ylmethoxy)carbonyl)-L-methionine;SCHEMBL4600701;2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methylsulfanyl-butyric acid;DTXSID50275948;DTXSID201315844;STR07776;AKOS001309879;AKOS017278311;AB01606;NSC 334292;NSC-334292;SY036880;SY059956;FT-0626506;FT-0629920;FT-0658739;FT-0686524;EN300-20840;AB00982875-01;A802669;A802681;N-{[(9H-Fluoren-9-yl)methoxy]carbonyl}methionine;Z104483548

Chemical Property of N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-methionine

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 371.11912932
• Heavy Atom Count: 26
• Complexity: 478

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSCCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Technology Process of N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-methionine

There total 6 articles about N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-methionine 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: 94.0%

9-fluorenylmethyl 4,6-dimethoxy-1,3,5-triazinyl carbonate (909114-66-5) + DL-methionine (59-51-8,26062-47-5,58576-49-1) → N-Fmoc-methionine (144701-23-5)

Guidance literature:

With sodium carbonate; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1055/s-2006-942389

Reference yield:

N-Fmoc-methionine (144701-23-5) → N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine (71989-28-1) + Nα-fluorenyl-9-methoxycarbonyl-D-Met (71989-28-1,144701-23-5,112883-40-6)

Guidance literature:

With trifluoroacetic acid; In hexane; isopropyl alcohol; at 25 ℃; Reagent/catalyst; Resolution of racemate;

DOI:10.1002/bkcs.11694

Reference yield:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) → N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine (71989-28-1) + Nα-fluorenyl-9-methoxycarbonyl-D-Met (71989-28-1,144701-23-5,112883-40-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium carbonate / water; 1,4-dioxane / Cooling with ice

1.2: 5 h / 20 °C

2.1: trifluoroacetic acid / isopropyl alcohol; hexane / 25 °C / Resolution of racemate

With sodium carbonate; trifluoroacetic acid; In 1,4-dioxane; hexane; water; isopropyl alcohol;

DOI:10.1002/bkcs.11694

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

DL-methionine

9-fluorenylmethyl 4,6-dimethoxy-1,3,5-triazinyl carbonate

Downstream raw materials:

O-W-F-I-M-H(1-Bzl)-NH₂

O-W-M-I-F-H(1-Bzl)-NH₂

O-W-F-M-F-H(1-Bzl)-NH₂

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine