3-[Nitroso(benzyloxy)amino]-N-[(benzyloxy)carbonyl]-L-alanine

Base Information

• Chemical Name: 3-[Nitroso(benzyloxy)amino]-N-[(benzyloxy)carbonyl]-L-alanine
• CAS No.: 832090-73-0
• Molecular Formula: C₁₈H₁₉N₃O₆
• Molecular Weight: 373.365
• Mol file: 832090-73-0.mol

Synonyms:3-[Nitroso(benzyloxy)amino]-N-[(benzyloxy)carbonyl]-L-alanine;

Chemical Property of 3-[Nitroso(benzyloxy)amino]-N-[(benzyloxy)carbonyl]-L-alanine

Chemical Property:

• Melting Point: 79-80 °C(Solv: ethyl ether (60-29-7))
• PKA: 3.37±0.10(Predicted)
• PSA: 117.53000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 2.87210
• Solubility.: Acetone, Chloroform, Dichloromethane

Purity/Quality:

98.5% ^*data from raw suppliers

3-[Nitroso(benzyloxy)amino]-N-[(benzyloxy)carbonyl]-L-alanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate for synthesis of L-Alanosine.

Technology Process of 3-[Nitroso(benzyloxy)amino]-N-[(benzyloxy)carbonyl]-L-alanine

There total 5 articles about 3-[Nitroso(benzyloxy)amino]-N-[(benzyloxy)carbonyl]-L-alanine 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: 99.0%

(S)-3-[(phenylmethyloxy)amino]-N-[(phenylmethyloxy)carbonyl]alanine (337368-14-6,96521-76-5) → (S)-3-[nitroso(phenylmethyloxy)amino]-N-[(phenylmethyloxy)carbonyl]alanine (832090-73-0,1286490-16-1)

Guidance literature:

With n-Butyl nitrite; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/ejoc.200400508

Reference yield:

N-(benzyloxycarbonyl)-L-serine (1145-80-8) → (S)-3-[nitroso(phenylmethyloxy)amino]-N-[(phenylmethyloxy)carbonyl]alanine (832090-73-0,1286490-16-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / DCC / acetonitrile / 0 - 20 °C

2: 87 percent / PPh₃; Et₃N / acetonitrile; CCl₄ / 24 h / 20 °C

3: 99 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 20 °C

4: 99 percent / nBuONO / CH₂Cl₂ / 1 h / 20 °C

With lithium hydroxide; n-Butyl nitrite; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1002/ejoc.200400508

Reference yield:

N-benzyloxyamine (622-33-3) → (S)-3-[nitroso(phenylmethyloxy)amino]-N-[(phenylmethyloxy)carbonyl]alanine (832090-73-0,1286490-16-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / DCC / acetonitrile / 0 - 20 °C

2: 87 percent / PPh₃; Et₃N / acetonitrile; CCl₄ / 24 h / 20 °C

3: 99 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 20 °C

4: 99 percent / nBuONO / CH₂Cl₂ / 1 h / 20 °C

With lithium hydroxide; n-Butyl nitrite; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1002/ejoc.200400508

upstream raw materials:

(S)-3-[(phenylmethyloxy)amino]-N-[(phenylmethyloxy)carbonyl]alanine

N-benzyloxyamine

N-(benzyloxycarbonyl)-L-serine

(S)-{2-[(phenylmethyloxy)amino]-1-(hydroxymethyl)-2-oxoethyl}carbamic acid phenylmethyl ester

Downstream raw materials:

Alanosine