Carbamic acid, [(hydroxyphosphinyl)methyl]-, phenylmethyl ester

Base Information

• Chemical Name: Carbamic acid, [(hydroxyphosphinyl)methyl]-, phenylmethyl ester
• CAS No.: 131066-43-8
• Molecular Formula: C9H12NO4P
• Molecular Weight: 229.172
• DSSTox Substance ID: DTXSID30422832
• Wikidata: Q82234887
• ChEMBL ID: CHEMBL1525927
• Mol file: 131066-43-8.mol

Synonyms:SMR000040965;131066-43-8;Carbamic acid, [(hydroxyphosphinyl)methyl]-, phenylmethyl ester;MLS000038573;MLS004256543;CHEMBL1525927;DTXSID30422832;HMS2170P15;HMS3311O11;STK538235;AKOS005468804;({[(benzyloxy)carbonyl]amino}methyl)phosphinic acid

Chemical Property of Carbamic acid, [(hydroxyphosphinyl)methyl]-, phenylmethyl ester

Chemical Property:

• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 228.04256983
• Heavy Atom Count: 15
• Complexity: 228

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Carbamic acid, [(hydroxyphosphinyl)methyl]-, phenylmethyl ester

There total 2 articles about Carbamic acid, [(hydroxyphosphinyl)methyl]-, phenylmethyl ester 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: 67.0%

aminomethyl-bis(H-phosphinic acid) (996-28-1) + benzyl chloroformate (501-53-1,94274-21-2) → N-benzyloxycarbonylaminomethyl-H-phosphinic acid (131066-43-8)

Guidance literature:

With potassium carbonate; In water; at 0 - 20 ℃; for 15h;

DOI:10.1021/jm800570q

Reference yield:

aminomethylphosphinate hydrochloride + benzyl chloroformate (501-53-1,94274-21-2) → N-benzyloxycarbonylaminomethyl-H-phosphinic acid (131066-43-8)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 3h; pH=10;

DOI:10.1021/jm050474e

Reference yield: 96.0%

ethyl 2-isobutylacrylate (87438-94-6) + N-benzyloxycarbonylaminomethyl-H-phosphinic acid (131066-43-8) → P-(Benzyloxycarbonylaminomethyl)-P-(ethyl 2-isobutylpropionate-3-yl)phosphinic acid (122624-57-1)

Guidance literature:

N-benzyloxycarbonylaminomethyl-H-phosphinic acid; With 1,1,1,3,3,3-hexamethyl-disilazane; at 115 ℃; for 2h;

ethyl 2-isobutylacrylate; at 90 ℃; for 3.5h;

DOI:10.1002/(SICI)1521-3765(19991001)5:10<2877::AID-CHEM2877>3.0.CO;2-Z

upstream raw materials:

aminomethyl-bis(H-phosphinic acid)

benzyl chloroformate

Downstream raw materials:

methyl N-benzyloxycarbonylaminomethylphosphinate

P-(Benzyloxycarbonylaminomethyl)-P-(ethyl 2-isobutylpropionate-3-yl)phosphinic acid

4-(methoxycarbonyl)tetrahydro-1,3-oxazin-2-one

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

Refernces

• 1、 Berlicki, ?ukasz,Obojska, Agnieszka,Forlani, Giuseppe,Kafarski, Pawel. "Design, synthesis, and activity of analogues of phosphinothricin as inhibitors of glutamine synthetase". . p. 6340 - 6349. Retrieved 2007/10/03.