L-Glutamic acid, 4,4-dimethyl-N-(triphenylmethyl)-, 1-(1,1-dimethylethyl) 5-(2-propenyl) ester

Base Information

• Chemical Name: L-Glutamic acid, 4,4-dimethyl-N-(triphenylmethyl)-, 1-(1,1-dimethylethyl) 5-(2-propenyl) ester
• CAS No.: 158805-11-9
• Molecular Formula: C33H39NO4
• Molecular Weight: 513.677
• Mol file: 158805-11-9.mol

Synonyms:

Chemical Property of L-Glutamic acid, 4,4-dimethyl-N-(triphenylmethyl)-, 1-(1,1-dimethylethyl) 5-(2-propenyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Glutamic acid, 4,4-dimethyl-N-(triphenylmethyl)-, 1-(1,1-dimethylethyl) 5-(2-propenyl) ester

There total 1 articles about L-Glutamic acid, 4,4-dimethyl-N-(triphenylmethyl)-, 1-(1,1-dimethylethyl) 5-(2-propenyl) 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:

(S)-2-Methyl-4-(trityl-amino)-pentanedioic acid 1-allyl ester 5-tert-butyl ester (189507-57-1) + methyl iodide (74-88-4) → (S)-2,2-Dimethyl-4-(trityl-amino)-pentanedioic acid 1-allyl ester 5-tert-butyl ester (158805-11-9)

Guidance literature:

With potassium hexamethylsilazane; Yield given. Multistep reaction; 1.) THF, -78 deg C, 55 min, 2.) THF, -78 deg C, 2 h;

DOI:10.1021/jm960878u

Reference yield: 97.0%

(S)-2,2-Dimethyl-4-(trityl-amino)-pentanedioic acid 1-allyl ester 5-tert-butyl ester (158805-11-9) → (S)-2,2-Dimethyl-4-(trityl-amino)-pentanedioic acid 5-tert-butyl ester (158805-16-4)

Guidance literature:

With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; for 0.333333h; Ambient temperature;

DOI:10.1021/jm960878u

Reference yield:

(S)-2,2-Dimethyl-4-(trityl-amino)-pentanedioic acid 1-allyl ester 5-tert-butyl ester (158805-11-9) → (S)-2-((S)-4-Carboxy-2,2-dimethyl-4-{4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-pentanedioic acid

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / Pd(PPh₃)4, pyrrolidine / CH₂Cl₂ / 0.33 h / Ambient temperature

2: 42 percent / PyBOP, DIEA, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

3: 98 percent / H₂ / 10percent Pd/C / ethyl acetate / 42 h / Ambient temperature

4: 58 percent / DEPC, Et₃N / dimethylformamide / 1.) 0 deg C, 10 min, 2.) RT, 2 h

5: 82 percent / TFA / 1.25 h / Ambient temperature

With pyrrolidine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; diethyl dicarbonate; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm960878u

upstream raw materials:

(S)-2-Methyl-4-(trityl-amino)-pentanedioic acid 1-allyl ester 5-tert-butyl ester

methyl iodide

Downstream raw materials:

(S)-2,2-Dimethyl-4-(trityl-amino)-pentanedioic acid 5-tert-butyl ester

(S)-2-[(S)-4-tert-Butoxycarbonyl-2,2-dimethyl-4-(trityl-amino)-butyrylamino]-pentanedioic acid di-tert-butyl ester

(S)-2-((S)-4-tert-Butoxycarbonyl-2,2-dimethyl-4-{4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-pentanedioic acid di-tert-butyl ester

Refernces