L-Glutamic acid, N-[(phenylmethoxy)carbonyl]-, 5-(1,1-dimethylethyl) 1-ethyl ester

Base Information

• Chemical Name: L-Glutamic acid, N-[(phenylmethoxy)carbonyl]-, 5-(1,1-dimethylethyl) 1-ethyl ester
• CAS No.: 3967-19-9
• Molecular Formula: C19H27NO6
• Molecular Weight: 365.426
• Mol file: 3967-19-9.mol

Synonyms:5-(tert-butyl)-1-ethyl-(2S)-2-{[(benzyloxy) carbonyl]amino}pentanedioate;(S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-tert-butyl ester 1-ethyl ester;

Chemical Property of L-Glutamic acid, N-[(phenylmethoxy)carbonyl]-, 5-(1,1-dimethylethyl) 1-ethyl ester

Chemical Property:

• Boiling Point: 483.0±45.0 °C(Predicted)
• PSA: 90.93000
• Density: 1.129±0.06 g/cm3(Predicted)
• LogP: 3.35730

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Glutamic acid, N-[(phenylmethoxy)carbonyl]-, 5-(1,1-dimethylethyl) 1-ethyl ester

There total 6 articles about L-Glutamic acid, N-[(phenylmethoxy)carbonyl]-, 5-(1,1-dimethylethyl) 1-ethyl 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: 83.0%

ethanol (64-17-5) + 5-tert-butyl N-benzyloxycarbonyl-L-glutamate (3886-08-6) → (S)-2-benzyloxycarbonylaminopentanedioic acid 5-tert-butyl ester 1-ethyl ester (3967-19-9)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1021/jm030354b

Reference yield: 78.0%

ethanol (64-17-5) + 4(S)-(2-tert-butoxycarbonylethyl)-5-oxo-oxazolidine 3-carboxylic acid benzyl ester (23632-68-0) → (S)-2-benzyloxycarbonylaminopentanedioic acid 5-tert-butyl ester 1-ethyl ester (3967-19-9)

Guidance literature:

With sodium hydrogencarbonate; for 0.166667h; Heating;

DOI:10.1016/S0040-4039(01)00971-6

Reference yield:

5-tert-butyl N-benzyloxycarbonyl-L-glutamate (3886-08-6) → 5-tert-butyl 1-ethyl 2-{[(benzyloxy)carbonyl]amino}pentanedioate (3967-19-9)

Guidance literature:

Multi-step reaction with 2 steps

1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide / dichloromethane / 0.17 h / 20 °C

2: copper(l) chloride / acetonitrile

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; copper(l) chloride; In dichloromethane; acetonitrile;

DOI:10.1002/ejoc.201402843

upstream raw materials:

bispicolyl amide γ-tert-butyl Z-L-glutamate

benzyl alcohol

5-tert-butyl N-benzyloxycarbonyl-L-glutamate

ethanol

Downstream raw materials:

ethyl 2(S)-2-{[(benzyloxy)carbonyl]amino}-5-oxo-5-[9-(4-pyridyl)-3,9-diazaspiro [5.5]undec-3-yl]pentanoate

(4S)-4-{[(4-methylphenyl)sulfonyl]amino}-5-ethoxy-5-oxopentanoic acid

(S)-2-(n-butoxycarbonylamino)-5-[2-(4-carbamimidoylphenyl)-1-oxo-2,8-diazaspiro[4.5]dec-8-yl]-5-oxopentanoic acid ethyl ester

(S)-5-{2-[4-(aminohydroxyaminomethyl)phenyl]-1-oxo-2,8-diazaspiro[4.5]dec-8-yl}-2-(n-butoxycarbonylamino)-5-oxopentanoic acid ethyl ester