[1-[[(Phenylmethoxy)carbonyl]amino]ethyl]phosphinic acid

Base Information

• Chemical Name: [1-[[(Phenylmethoxy)carbonyl]amino]ethyl]phosphinic acid
• CAS No.: 108327-37-3
• Molecular Formula: C10H14NO4P
• Molecular Weight: 243.199
• DSSTox Substance ID: DTXSID70445444
• Mol file: 108327-37-3.mol

Synonyms:108327-37-3;(R)-1-(N-benzyloxycarbonylamino)ethylphosphinic acid;[1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinic acid;MLS004256556;SCHEMBL6926649;DTXSID70445444;KHVQOUDIMLMPNA-UHFFFAOYSA-N;115115-40-7;SMR003081575;(1-{[(Benzyloxy)carbonyl]amino}ethyl)(hydroxy)oxophosphanium

Chemical Property of [1-[[(Phenylmethoxy)carbonyl]amino]ethyl]phosphinic acid

Chemical Property:

• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 242.05821989
• Heavy Atom Count: 16
• Complexity: 253

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(NC(=O)OCC1=CC=CC=C1)[P+](=O)O

Technology Process of [1-[[(Phenylmethoxy)carbonyl]amino]ethyl]phosphinic acid

There total 3 articles about [1-[[(Phenylmethoxy)carbonyl]amino]ethyl]phosphinic acid 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: 91.0%

(1-aminoethyl)phosphinic acid (74333-44-1) + benzyl chloroformate (501-53-1,94274-21-2) → [1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinic acid (108327-37-3)

Guidance literature:

(1-aminoethyl)phosphinic acid; benzyl chloroformate; With sodium hydroxide; In water; at 0 ℃; for 1h;

With hydrogenchloride; In water; Cooling with ice;

Reference yield: 85.0%

N-benzyloxycarbonylalanine (4132-86-9,26607-51-2,1142-20-7) → [1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinic acid (108327-37-3)

Guidance literature:

N-benzyloxycarbonylalanine; With methanol; at 10 ℃; Electrolysis;

With triphenylphosphonium tetrafluoroborate; In dichloromethane; at 20 ℃; for 0.5h;

With bis(trimethylsilyl)phosphonite; methyl-triphenylphosphonium iodide; N-ethyl-N,N-diisopropylamine; at 60 ℃; for 24h;

DOI:10.1016/j.molcatb.2016.05.011

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) + (1-amino-ethyl)-phosphinic acid; hydrobromide → [1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinic acid (108327-37-3)

Guidance literature:

With aq. base;

DOI:10.1039/b003848m

upstream raw materials:

(1-aminoethyl)phosphinic acid

benzyl chloroformate

N-benzyloxycarbonylalanine

Downstream raw materials:

(1R)-(-)-1-aminoethylphosphinic acid

C₃₃H₃₄NO₆P

2-[(Adamantan-1-yloxy)-(1-benzyloxycarbonylamino-ethyl)-phosphinoylmethyl]-4-methyl-pentanoic acid ethyl ester

2-[(Adamantan-1-yloxy)-(1-benzyloxycarbonylamino-ethyl)-phosphinoylmethyl]-4-methyl-pentanoic acid

Refernces

• 1、 Zielińska, Katarzyna,Mazurkiewicz, Roman,Szymańska, Katarzyna,Jarz?bski, Andrzej,Magiera, Sylwia,Erfurt, Karol. "Penicillin G acylase-mediated kinetic resolution of racemic 1-(N-acylamino)alkylphosphonic and 1-(N-acylamino)alkylphosphinic acids and their esters". . p. 31 - 40. Retrieved 2016/07/19.
• 2、 Strancar, Katja,Blanot, Didier,Gobec, Stanislav. "Design, synthesis and structure-activity relationships of new phosphinate inhibitors of MurD". . p. 343 - 348. Retrieved 2007/10/03.