* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Stage #1: glycylglycine benzyl ester p-toluene sulfonate salt With triethylamine In dichloromethane at 20℃; for 0.166667h;
Stage #2: succinic acid anhydride In dichloromethane for 24h;
{2-[3-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylcarbamoyl)-2-tert-butoxycarbonylamino-propionylamino]-acetylamino}-acetic acid benzyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With 4-methyl-morpholine; benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 24℃; for 4.5h;
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; for 49h;
92%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane
Stage #1: dioctadecylcarbamoylmethoxyacetic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h;
Stage #2: glycylglycine benzyl ester p-toluene sulfonate salt With triethylamine In dichloromethane at 20℃;
With 4-methyl-morpholine; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 48h;
Stage #1: dipropylcarbamoylmethoxyacetic acid With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;
Stage #2: glycylglycine benzyl ester p-toluene sulfonate salt With 4-methyl-morpholine In dichloromethane at 20℃;
Stage #1: dioctadecylaminoacetic acid With benzotriazol-1-ol; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In dichloromethane at 20℃; for 0.5h;
Stage #2: glycylglycine benzyl ester p-toluene sulfonate salt With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 48h; Further stages.;
[2-(2-[1-(2-{2-[2-(2-dipropylcarbamoylmethoxyacetylamino)acetylamino]acetylamino}acetyl)pyrrolidine-2-carbonyl]amino}dideuterioacetylamino)acetylamino]acetic acid benzyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Multi-step reaction with 5 steps
1.1: 0.37 g / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; NMM / CH2Cl2 / 48 h / 20 °C
2.1: aq. HCl / dioxane / 0.5 h / 5 °C
3.1: 42 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; NMM / CH2Cl2 / 20 °C
4.1: HCl / dioxane / 0.5 h / 5 °C
5.1: PyBroP; 1-hydroxybenzotriazole / CH2Cl2 / 0.5 h
5.2: 80 percent / DIEA / CH2Cl2 / 48 h / 20 °C
Stage #1: C33H29F2NO6; glycylglycine benzyl ester p-toluene sulfonate salt With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine
Stage #2: With hydrogen
In the scheme shown below an amino acid containing compound is described. Coupling of 105A with benzyl glycyl glycinate tosylate in the presence of triethylamine and EDCI to provide the corresponding amide that is deprotected by hydrogenation over palladium on carbon to give the desired product 109A. EPO
Stage #1: C26H24FNO5; glycylglycine benzyl ester p-toluene sulfonate salt With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine
Stage #2: With hydrogen
In the scheme shown below an amino acid containing compound is described. Coupling of 117A with benzyl glycyl glycinate tosylate in the presence of triethylamine and EDCI to provide the corresponding amide that is deprotected by hydrogenation over palladium on carbon to give the desired product 121A.
Stage #1: C33H30FNO6; glycylglycine benzyl ester p-toluene sulfonate salt With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine
Stage #2: With hydrogen
In the scheme shown below an amino acid containing compound is described. Coupling of 127A with benzyl glycyl glycinate tosylate in the presence of triethylamine and EDCI to provide the corresponding amide that is deprotected by hydrogenation over palladium on carbon to give the desired product 131A.
carbonyl(pentamethylcyclopentadienyl)cobalt diiodide[ No CAS ]
[ 1738-82-5 ]
{(η5-C5Me5)CoI(glycylglycinebenzylester)}I[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
62%
With KOH In methanol byproducts: potassium chloride; under Ar, stirred for 15 h; centrifuged, evapd. to dryness in vac., residue stirred in CH2Cl2, KCl sepd. by centrifugation, addn. of pentane with stirring, ppt. isolated, dried in vac. at 80°C for several days; elem. anal.;
dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer[ No CAS ]
[ 124-41-4 ]
[ 1738-82-5 ]
(η5-C5Me5)RhCl(glycylglycinebenzylester(1-))[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
88%
In methanol byproducts: NaCl; under Ar, dropwise addn. of 4 equivalents NaOMe-soln. to Rh-compd. and 2 equivalents of ligand in methanol, stirred for 15 min at room temp.; evapd. in vac., residue taken up in CH2Cl2, centrifuged (NaCl), crystd. (CH2Cl2/hexane), dried (2 h, 60°C); elem. anal.;
Stage #1: glycylglycine benzyl ester p-toluene sulfonate salt With triethylamine In dichloromethane at 20℃; for 0.166667h;
Stage #2: 3-(1-nitro-2-phenylethylidene)oxetane In dichloromethane at -78 - 20℃;