3-(4-Bromophenyl)-2-({[(9H-fluoren-9-yl)methoxy](hydroxy)methylidene}amino)propanoate

Base Information

• Chemical Name: 3-(4-Bromophenyl)-2-({[(9H-fluoren-9-yl)methoxy](hydroxy)methylidene}amino)propanoate
• CAS No.: 198561-04-5
• Molecular Formula: C₂₄H₂₀BrNO₄
• Molecular Weight: 466.331
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID30941694
• Wikidata: Q72478169
• Mol file: 198561-04-5.mol

Synonyms:DTXSID30941694;3-(4-Bromophenyl)-2-({[(9H-fluoren-9-yl)methoxy](hydroxy)methylidene}amino)propanoate

Chemical Property of 3-(4-Bromophenyl)-2-({[(9H-fluoren-9-yl)methoxy](hydroxy)methylidene}amino)propanoate

Chemical Property:

• Appearance/Colour: off-white to light yellow crystalline powder
• Vapor Pressure: 2.31E-18mmHg at 25°C
• Melting Point: 151.5 °C
• Refractive Index: 1.6500 (estimate)
• Boiling Point: 660.8 °C at 760 mmHg
• PKA: 3.72±0.10(Predicted)
• Flash Point: 353.4 °C
• PSA: 75.63000
• Density: 1.459 g/cm³
• LogP: 5.37440
• Storage Temp.: Store at 0°C
• XLogP3: 6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 464.04975
• Heavy Atom Count: 30
• Complexity: 579

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-l-4-bromophenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC=C(C=C4)Br)C(=O)[O-]
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC4=CC=C(C=C4)Br)C(=O)[O-]

Technology Process of 3-(4-Bromophenyl)-2-({[(9H-fluoren-9-yl)methoxy](hydroxy)methylidene}amino)propanoate

There total 1 articles about 3-(4-Bromophenyl)-2-({[(9H-fluoren-9-yl)methoxy](hydroxy)methylidene}amino)propanoate 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: 97.0%

H-p-BrPhe-OH (24250-84-8) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → Fmoc-4-bromo-L-phenylalanine (198561-04-5)

Guidance literature:

With sodium carbonate; In water; acetone; at 20 ℃; for 2h;

DOI:10.1002/anie.201812348

Reference yield: 10.0%

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Leu-OH (35661-60-0) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3,136132-75-7) + N-Fmoc L-Phe (35661-40-6) + Fmoc-Ser(tBu)-OH (71989-33-8) + Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) + Fmoc-L-Gln(Trt)-OH (132327-80-1,200623-62-7) + Fmoc-Arg(Pbf)-OH (119831-72-0,157774-30-6) + Fmoc-His(Trt)-OH (109425-51-6) + Fmoc-(S)-2-aminohexanoic acid (77284-32-3,144701-20-2) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-α-aminoisobutyric acid (94744-50-0) + Fmoc-4-bromo-L-phenylalanine (198561-04-5) → AFRRQRPRLSHKGPNleAibBrF

Guidance literature:

Fmoc-L-4-bromophenylalanine-OH; With N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 2.5h; Inert atmosphere;

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

N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; N-Fmoc L-Phe; Fmoc-Ser(tBu)-OH; Fmoc-Lys(tert-butoxycarbonyl); Fmoc-L-Gln(Trt)-OH; Fmoc-Arg(Pbf)-OH; Fmoc-His(Trt)-OH; Fmoc-(S)-2-aminohexanoic acid; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-α-aminoisobutyric acid; Further stages;

DOI:10.1021/acs.jmedchem.0c01395

Reference yield: 9.5%

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Leu-OH (35661-60-0) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3,136132-75-7) + N-Fmoc L-Phe (35661-40-6) + Fmoc-Ser(tBu)-OH (71989-33-8) + Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) + Fmoc-L-Gln(Trt)-OH (132327-80-1,200623-62-7) + Fmoc-Arg(Pbf)-OH (119831-72-0,157774-30-6) + Fmoc-His(Trt)-OH (109425-51-6) + Fmoc-(S)-2-aminohexanoic acid (77284-32-3,144701-20-2) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-α-aminoisobutyric acid (94744-50-0) + Fmoc-4-bromo-L-phenylalanine (198561-04-5) → KFARQRPRLSHKGPNleAibBrF

Guidance literature:

Fmoc-L-4-bromophenylalanine-OH; With N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 2.5h; Inert atmosphere;

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

N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; N-Fmoc L-Phe; Fmoc-Ser(tBu)-OH; Fmoc-Lys(tert-butoxycarbonyl); Fmoc-L-Gln(Trt)-OH; Fmoc-Arg(Pbf)-OH; Fmoc-His(Trt)-OH; Fmoc-(S)-2-aminohexanoic acid; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-α-aminoisobutyric acid; Further stages;

DOI:10.1021/acs.jmedchem.0c01395

upstream raw materials:

H-p-BrPhe-OH

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

Downstream raw materials:

Cph-Cha-Dap-Glu-Bph-Leu

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-4-bromo-L-phenylalanine

9H-fluoren-9-ylmethyl (S)-4-(4-bromo)-benzyl-5-oxo-1,3-oxazolidine-3-carboxylate

Refernces