Carbamic acid, (tetrahydro-5-oxo-3-furanyl)-, phenylmethyl ester (9CI)

Base Information

• Chemical Name: Carbamic acid, (tetrahydro-5-oxo-3-furanyl)-, phenylmethyl ester (9CI)
• CAS No.: 305859-68-1
• Molecular Formula: C12H13 N O4
• Molecular Weight: 235.24
• Hs Code.: 2932190090
• Mol file: 305859-68-1.mol

Synonyms:Carbamic acid, (tetrahydro-5-oxo-3-furanyl)-, phenylmethyl ester (9CI)

Chemical Property of Carbamic acid, (tetrahydro-5-oxo-3-furanyl)-, phenylmethyl ester (9CI)

Chemical Property:

• PSA: 68.12000
• LogP: 1.43270

Purity/Quality:

NLT 98% ^*data from raw suppliers

(5-Oxo-tetrahydro-furan-3-yl)-carbamicacidbenzylester 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Carbamic acid, (tetrahydro-5-oxo-3-furanyl)-, phenylmethyl ester (9CI)

There total 4 articles about Carbamic acid, (tetrahydro-5-oxo-3-furanyl)-, phenylmethyl ester (9CI) 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: 65.0%

benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamate (35739-00-5) → (R,S)-4-benzyloxycarbonylamino-4,5-dihydro-2(3H)-furanone (305859-68-1)

Guidance literature:

benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamate; With sodium tetrahydroborate; In tetrahydrofuran; at 0 ℃; for 3.5h;

With hydrogenchloride; In tetrahydrofuran; water; pH=~ 2;

With toluene-4-sulfonic acid; In benzene; for 3h; Heating / reflux;

Reference yield: 43.0%

N-(Benzyloxycarbonyl)-3-amino-1-cyclobutanone (130369-36-7) → (R,S)-4-benzyloxycarbonylamino-4,5-dihydro-2(3H)-furanone (305859-68-1)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 20h;

DOI:10.1016/j.tet.2015.12.071

Reference yield:

(S)-2-(((benzyloxy)carbonyl)amino)butanoic acid (42918-86-5,1145-79-5,2900-20-1,20395-87-3) → (R,S)-4-benzyloxycarbonylamino-4,5-dihydro-2(3H)-furanone (305859-68-1)

Guidance literature:

With hydrogenchloride; sodium borohydrid; acetic anhydride; toluene-4-sulfonic acid; In tetrahydrofuran; water; benzene;

upstream raw materials:

(+/-)-4-Amino-4,5-dihydro-2(3H)-furanone

benzyl chloroformate

benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamate

(S)-2-(((benzyloxy)carbonyl)amino)butanoic acid

Downstream raw materials:

(-)-kainic acid

methyl (3S)-3-[[(benzyloxy)carbonyl]amino]-4-hydroxybutanoate

Refernces

• 1、 -. "CERTAIN CHEMICAL ENTITIES, COMPOSITIONS, AND METHODS". Page/Page column 57. . Retrieved 2010/11/27.
• 2、 El Hadri, Ahmed,Abouabdellah, Ahmed,Thomet, Urs,Baur, Roland,Furtmüller, Roman,Sigel, Erwin,Sieghart, Werner,Dodd, Robert H.. "N-substituted 4-amino-3,3-dipropyl-2(3H)-furanones: New positive allosteric modulators of the GABAA receptor sharing electrophysiological properties with the anticonvulsant loreclezole". . p. 2824 - 2831. Retrieved 2007/10/03.