CMDA

Base Information

• Chemical Name: CMDA
• CAS No.: 122665-73-0
• Molecular Formula: C17H23ClN2O8S
• Molecular Weight: 450.897
• Hs Code.: 2924299090
• Mol file: 122665-73-0.mol

Synonyms:(2S)-2-({4-[(2-chloroethyl)[2-(methanesulfonyloxy)ethyl]amino]phenyl}formamido)pentanedioic acid;CMDA;N-4-[(2-Chloroethyl)(2-mesyloxyethyl)amino]benzoyl-L-glutamicacid;2-{4-[(2-Chloro-ethyl)-(2-methanesulfonyloxy-ethyl)-amino]-benzoylamino}-pentanedioic acid;2-{4-[(S)-(2-Chloro-ethyl)-(2-methanesulfonyloxy-ethyl)-amino]-benzoylamino}-pentanedioic acid;L-Glutamic acid, N-(4-((2-chloroethyl)(2-((methylsulfonyl)oxy)ethyl)amino)benzoyl)-;4-Cema-benzoyl-glutamic acid;

Chemical Property of CMDA

Chemical Property:

• Vapor Pressure: 2.3E-24mmHg at 25°C
• Refractive Index: 1.581
• Boiling Point: 761.3 °C at 760 mmHg
• PKA: 3.48±0.10(Predicted)
• Flash Point: 414.2 °C
• PSA: 158.69000
• Density: 1.446 g/cm³
• LogP: 2.22750
• Storage Temp.: 2-8°C

Purity/Quality:

99%, ^*data from raw suppliers

(S)-2-(4-((2-Chloroethyl)(2-((methylsulfonyl)oxy)ethyl)amino)benzamido)pentanedioicacid 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of CMDA

There total 14 articles about CMDA 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: 82.0%

di-tert-butyl 4-<(2-chloroethyl)<2-(mesyloxy)ethyl>amino>benzoyl-L-glutamate (123724-56-1) → CMDA (122665-73-0)

Guidance literature:

With trifluoroacetic acid; for 0.5h; Ambient temperature;

DOI:10.1021/jm00164a034

Reference yield:

L-glutamic acid di-tert-butyl ester hydrochloride (32677-01-3) → CMDA (122665-73-0)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂

2: H₂ / 10percent Pd/C

3: 78 percent / acetic acid / 48 h / Ambient temperature

4: 0.3 percent / pyridine / 1.) 2 deg C, 20 min, 2.) 80 deg C, 80 min

5: 82 percent / trifluoroacetic acid / 0.5 h / Ambient temperature

With pyridine; hydrogen; acetic acid; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane;

DOI:10.1021/jm00164a034

Reference yield:

Di-tert-butyl 4-nitrobenzoyl-L-glutamate (88050-23-1) → 4-<(2-Chloroethyl)(2-mesyloxyethyl)amino>benzoyl-L-glutamic acid (122665-73-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / ammonium formate / 10percent Pd/C / methanol / 0.5 h / Ambient temperature

2: 6N aq. HCl, NaCNBH₃ / methanol; H₂O / 120 h / Ambient temperature

3: 65 percent / glacial acetic acid / 48 h / Ambient temperature

4: 75 percent / NEt₃ / CH₂Cl₂ / 1 h / 5 °C

5: 2.40 g / HCOOH / 48 h / 10 °C

With hydrogenchloride; formic acid; ammonium formate; sodium cyanoborohydride; acetic acid; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; water;

DOI:10.1016/S0040-4020(01)87844-3

upstream raw materials:

di-tert-butyl 4-<(2-chloroethyl)<2-(mesyloxy)ethyl>amino>benzoyl-L-glutamate

di-tert-butyl (S)-N-(p-aminobenzoyl)-glutamate

di-tert-butyl (S)-N-(p-nitrobenzoyl)-glutamate

L-glutamic acid di-tert-butyl ester hydrochloride

Downstream raw materials:

4-[(2-chloroethyl)-(2-mesyloxyethyl)amino]benzoic acid

L-glutamic acid

Refernces

• 1、 -. "Improvements relating to the production of prodrugs". . . Retrieved 2008/06/13.
• 2、 Mann, John,Haase-Held, Margret,Springer, Caroline J.,Bagshawe, Kenneth D.. "SYNTHESIS OF AN N-MUSTARD PRODRUG". . p. 5377 - 5382. Retrieved 2007/10/02.