2-(Benzyloxycarbonylamino)-3-(4-hydroxyphenyl)propionic acid hydrazide

Base Information

• Chemical Name: 2-(Benzyloxycarbonylamino)-3-(4-hydroxyphenyl)propionic acid hydrazide
• CAS No.: 16679-95-1
• Molecular Formula: C17H19N3O4
• Molecular Weight: 329.356
• NSC Number: 88492
• Nikkaji Number: J2.327.784K
• Mol file: 16679-95-1.mol

Synonyms:Z-L-tyrosine hydrazide;NSC88492;NCIOpen2_009607;2-(Benzyloxycarbonylamino)-3-(4-hydroxyphenyl)propionic acid hydrazide;NSC-88492;benzyl N-[1-hydrazinyl-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]carbamate;CCG-233124;FT-0772440

Chemical Property of 2-(Benzyloxycarbonylamino)-3-(4-hydroxyphenyl)propionic acid hydrazide

Chemical Property:

• Vapor Pressure: 1.62E-17mmHg at 25°C
• Melting Point: 220 °C
• Refractive Index: 1.616
• Boiling Point: 650.4°C at 760 mmHg
• PKA: 9.81±0.15(Predicted)
• Flash Point: 347.2°C
• PSA: 113.68000
• Density: 1.3g/cm³
• LogP: 2.70170
• Storage Temp.: -15°C
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 329.13755610
• Heavy Atom Count: 24
• Complexity: 405

Purity/Quality:

99% ^*data from raw suppliers

(S)-Benzyl(1-hydrazinyl-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)carbamate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CC2=CC=C(C=C2)O)C(=O)NN

Technology Process of 2-(Benzyloxycarbonylamino)-3-(4-hydroxyphenyl)propionic acid hydrazide

There total 4 articles about 2-(Benzyloxycarbonylamino)-3-(4-hydroxyphenyl)propionic acid hydrazide 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: 85.0%

N-(benzyloxycarbonyl)-L-tyrosine methyl ester (13512-31-7) → benzyl (S)-(1-hydrazinyl-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)carbamate (16679-95-1)

Guidance literature:

With hydrazine hydrate; In methanol; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1039/d0cc02728f

Reference yield:

(2S)-3-(4-hydroxyphenyl)-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)propanoic acid (86099-14-1) → benzyl (S)-(1-hydrazinyl-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)carbamate (16679-95-1)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / Inert atmosphere

2: hydrazine hydrate / methanol / 12 h / 20 °C / Inert atmosphere

With thionyl chloride; hydrazine hydrate; In methanol;

DOI:10.1039/d0cc02728f

Reference yield:

N-[(phenylmethoxy)carbonyl]-L-tyrosine (16679-94-0) → benzyl (S)-(1-hydrazinyl-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)carbamate (16679-95-1)

Guidance literature:

With ethanol; hydrazine hydrate;

upstream raw materials:

N-[(phenylmethoxy)carbonyl]-L-tyrosine

(2S)-3-(4-hydroxyphenyl)-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)propanoic acid

N-(benzyloxycarbonyl)-L-tyrosine methyl ester

Downstream raw materials:

N-Carbobenzoxytyrosyl-S-benzylcysteine ethyl ester

Z-L-Tyr-Gly-OMe

N-(N-benzyloxycarbonyl-L-tyrosyl)-L-serine methyl ester

(S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-3-hydroxy-propionic acid methyl ester

Refernces