4816-80-2

Usage

Chemical Properties

white crystalline powder

Uses

Protected L-Glutamic Acid.

InChI:InChI=1/C12H15NO6S/c1-8-2-4-9(5-3-8)20(18,19)13-10(12(16)17)6-7-11(14)15/h2-5,10,13H,6-7H2,1H3,(H,14,15)(H,16,17)/t10-/m0/s1

Synthetic route

C20H31NO6S (55666-46-1) → N-tosyl-L-glutamic acid (4816-80-2)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃;	100%

L-glutamic acid (56-86-0) → N-tosyl-L-glutamic acid (4816-80-2)

Conditions	Yield
With sodium hydroxide In water at 70℃;	93%

L-glutamic acid (56-86-0) + p-toluenesulfonyl chloride (98-59-9) → N-tosyl-L-glutamic acid (4816-80-2)

Conditions	Yield
Stage #1: L-glutamic acid; p-toluenesulfonyl chloride With sodium hydroxide In water at 70℃; for 1.5h; Stage #2: With hydrogenchloride In water at 0℃; pH=3;	92%
Stage #1: L-glutamic acid; p-toluenesulfonyl chloride With sodium hydroxide at 70℃; Stage #2: With hydrogenchloride at 0℃; pH=~ 3;	92%
Stage #1: L-glutamic acid With sodium hydroxide at 25 - 30℃; Stage #2: p-toluenesulfonyl chloride at 70 - 75℃; pH=< 9;	76%

L-glutamic acid di-tert-butyl ester hydrochloride (32677-01-3) + p-toluenesulfonyl chloride (98-59-9) → N-tosyl-L-glutamic acid (4816-80-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 1 h 2: trifluoroacetic acid / dichloromethane / 20 °C View Scheme

dexmethylphenidate N-tosyl-l-glutamate Salt → N-tosyl-L-glutamic acid (4816-80-2)

Conditions	Yield
Stage #1: dexmethylphenidate N-tosyl-l-glutamate Salt With sodium hydrogencarbonate In ethyl acetate at 40℃; for 0.5h; Stage #2: With hydrogenchloride In water; iso-butanol at 10 - 40℃; for 0.5h;

ethanol (64-17-5) + N-tosyl-L-glutamic acid (4816-80-2) → N-[(4-methylphenyl)sulfonyl]-β-alanine ethyl ester (76616-47-2)

Conditions	Yield
With sulfuric acid Reflux;	95%

methyl 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetate (83881-46-3, 163837-44-3, 163837-46-5) + N-tosyl-L-glutamic acid (4816-80-2) → dextrorotatory methyl-2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetate N-[(4-methylphenyl)sulfonyl]-L-glutamate

Conditions	Yield
In water; isopropyl alcohol at 20 - 60℃; for 1h; Product distribution / selectivity;	90.7%
In water; isopropyl alcohol at 20 - 60℃; for 1h; Product distribution / selectivity;	63.9%

4,4'-bipyridine (553-26-4) + cobalt(II) nitrate hexahydrate + N-tosyl-L-glutamic acid (4816-80-2) → [Co((+)-N-p-tolylsulfonylglutamate)(4,4'-bipyridine)](n)*H2O

Conditions	Yield
In water High Pressure; mixing of Co(NO3)2*6H2O, N-p-tolylsulfonyl-L-glutamic acid and 4,4'-bipyin H2O in Teflon reactor, heating to 120°C for 3 d; slow cooling to room temp., crystn., elem. anal.;	89%

zinc(II) nitrate hexahydrate + N-tosyl-L-glutamic acid (4816-80-2) + trans-1,2-bis(4-pyridyl)ethylene (1135-32-6) → [Zn(1,2-bis(4-pyridyl)ethylene)(N-carbamyl-L-glutamate)2H2O]

Conditions	Yield
Stage #1: zinc(II) nitrate hexahydrate; trans-1,2-bis(4-pyridyl)ethylene In ethanol; water; N,N-dimethyl-formamide for 0.166667h; Stage #2: N-tosyl-L-glutamic acid With sodium hydroxide In ethanol; water; N,N-dimethyl-formamide for 730.5h;	83%

N-tosyl-L-glutamic acid (4816-80-2) + copper(II) acetate monohydrate (6046-93-1) → Cu(N-p-tolylsulfonyl-L-glutamate dianion)*H2O

Conditions	Yield
In ethanol; water addn. of hot aq. soln. of Cu-salt to EtOH soln. of ligand; crystn. on cooling to room temp.; elem. anal.;	80%

N-tosyl-L-glutamic acid (4816-80-2) → 2-(4'-methylbenzenesulfonyl)-L-glutamic acid dichloride (108590-52-9)

Conditions	Yield
With thionyl chloride for 0.5h; Heating;	79.7%
With diethyl ether; phosphorus pentachloride

N-tosyl-L-glutamic acid (4816-80-2) → 1-(4'-methylbenzenesulfonyl)-5-oxopyrrolidine-2-carboxylic acid (21957-65-3)

Conditions	Yield
With acetyl chloride for 2h; Heating;	74.46%
With dicyclohexyl-carbodiimide In dichloromethane Ambient temperature;	63%
With chloroform; phosphorus trichloride

4-(2-pyridyl)pyridine (581-47-5) + cobalt(II) nitrate hexahydrate + N-tosyl-L-glutamic acid (4816-80-2) → [Co((+)-N-p-tolylsulfonylglutamate)(2,4'-bipyridine)2(H2O)2](n)*5nH2O

Conditions	Yield
In water High Pressure; mixing of Co(NO3)2*6H2O, N-p-tolylsulfonyl-L-glutamic acid and 2,4'-bipyin H2O in Teflon reactor, heating to 120°C for 3 d; slow cooling to room temp., crystn., elem. anal.;	70.3%

cadmium(II) acetate hydrate + N-tosyl-L-glutamic acid (4816-80-2) → Cd2(N-p-tolylsulfonyl-L-glutamate dianion)2(H2O)6

Conditions	Yield
In ethanol; water addn. of aq. soln. of Cd-salt to EtOH soln. of ligand; crystn. on concn.; elem. anal.;	70%

zinc(II) acetate hydrate + N-tosyl-L-glutamic acid (4816-80-2) → [Zn(N-p-tolylsulfonyl-L-glutamate dianion)(H2O)2]*H2O

Conditions	Yield
In ethanol; water addn. of aq. soln. of Zn-salt to EtOH soln. of ligand; crystn. on concn.; elem. anal.;	70%

methanol (67-56-1) + N-tosyl-L-glutamic acid (4816-80-2) → dimethyl (2S)-2-{[(4-methylphenyl)sulfonyl]amino}pentane-1,5-dioate (95305-51-4)

Conditions	Yield
With sulfuric acid Reflux;	69%
With chloro-trimethyl-silane cooling;

4-(2-pyridyl)pyridine (581-47-5) + N-tosyl-L-glutamic acid (4816-80-2) + zinc(II) acetate dihydrate (5970-45-6) → [zinc(2,4'-bipyridine)(H2O)((+)-N-tosyl-L-glutamate)] (1431535-97-5)

Conditions	Yield
With sodium hydroxide In methanol; water for 0.166667h; pH=6;	68%

Methadone (76-99-3) + N-tosyl-L-glutamic acid (4816-80-2) → (6R)-6-(dimethylamino)-4,4-diphenyl-3-heptanone-(+)-N-tosyl glutamate salt

Conditions	Yield
In acetone at 25 - 55℃; Solvent;	66%

1,10-Phenanthroline (66-71-7) + N-tosyl-L-glutamic acid (4816-80-2) + water (7732-18-5) + zinc(II) acetate dihydrate (5970-45-6) → Zn2(N-tosyl-L-glutamic acid(-2H))2(1,10-phenanthroline)2(H2O)2

Conditions	Yield
With sodium fluoride at 120℃; for 120h;	65%

methanol (67-56-1) + 1,3-di(4-pyridyl)propane (17252-51-6) + N-tosyl-L-glutamic acid (4816-80-2) + zinc(II) acetate dihydrate (5970-45-6) → [Zn(C12H13NO6S-Me)2(1,3-bis(4-pyridyl)propane)2]

Conditions	Yield
With NaOH In methanol; water High Pressure; Zn compd., N-tosyl-L-glutamic acid, bpp, and NaOH (1:1:1:2 molar ratio) in H2O/MeOH (1/1) stirerd for 5 min; filtered, crystd. on storage at room temp. for 3 d, septd., elem. anal.;	62%

1,10-Phenanthroline (66-71-7) + N-tosyl-L-glutamic acid (4816-80-2) + zinc(II) acetate dihydrate (5970-45-6) → Zn2(N-tosyl-L-glutamic acid(-2H))2(1,10-phenanthroline)2

Conditions	Yield
With sodium fluoride In water at 120℃; for 120h;	61%

4,4'-bipyridine (553-26-4) + nickel(II) nitrate hexahydrate + N-tosyl-L-glutamic acid (4816-80-2) → [Ni((+)-N-p-tolylsulfonyl-L-glutamate)(4,4'-bipyridine)2(H2O)0.5](n)*0.5nH2O

Conditions	Yield
In water High Pressure; mixing of Ni(NO3)2*6H2O, N-p-tolylsulfonyl-L-glutamic acid and 4,4'-bipyin H2O in Teflon reactor, heating to 120°C for 3 d; slow cooling to room temp., crystn., elem. anal.;	56%

1H-imidazole (288-32-4) + N-tosyl-L-glutamic acid (4816-80-2) + zinc(II) acetate dihydrate (5970-45-6) → [zinc(imidazole)(H2O)((+)-N-tosyl-L-glutamate)] (1431535-96-4)

Conditions	Yield
With sodium hydroxide In methanol; water for 0.166667h; pH=6;	56%

1,10-Phenanthroline (66-71-7) + cadmium(II) nitrate tetrhydrate + N-tosyl-L-glutamic acid (4816-80-2) → C12H13NO6S(2-)*Cd(2+)*C12H8N2

Conditions	Yield
With sodium hydroxide In water at 140℃; for 168h; pH=5;	53.2%

N-tosyl-L-glutamic acid (4816-80-2) + copper(II) acetate monohydrate (6046-93-1) + potassium hydroxide → Cu(N-p-tolylsulfonyl-L-glutamate dianion)*H2O + K[Cu(N-p-tolylsulfonyl-L-glutamate trianion)]*3H2O

Conditions	Yield
In ethanol; water addn. of hot aq. soln. of Cu-salt to EtOH soln. of ligand, crystn. on cooling to room temp., collection of first product, addn. of KOH to filtrate to pH 9; pptn. on addn. of dioxane; elem. anal.;	A n/a B 50%

1H-imidazole (288-32-4) + cadmium(II) nitrate tetrhydrate + N-tosyl-L-glutamic acid (4816-80-2) → C12H13NO6S(2-)*Cd(2+)*H2O*C3H4N2

Conditions	Yield
With sodium hydroxide In water at 140℃; for 168h; pH=5;	47%

pyridin-3-ylamine (462-08-8) + cadmium(II) nitrate tetrhydrate + N-tosyl-L-glutamic acid (4816-80-2) → 2C12H13NO6S(2-)*2Cd(2+)*5C5H6N2*2.5H2O

Conditions	Yield
With sodium hydroxide In water at 140℃; for 168h; pH=5;	45.1%

methanol (67-56-1) + 1,3-di(4-pyridyl)propane (17252-51-6) + N-tosyl-L-glutamic acid (4816-80-2) + zinc(II) acetate dihydrate (5970-45-6) → [Zn(C12H13NO6S-Me)2(1,3-bis(4-pyridyl)propane)]

Conditions	Yield
With NaOH In methanol; water High Pressure; Zn compd., N-tosyl-L-glutamic acid, bpp, and NaOH (1:1:1:2 molar ratio) in H2O/MeOH (1/3) stirerd for 5 min; filtered, crystd. on storage at room temp. for 3 d, septd., elem. anal.;	45%

pyridin-3-ylamine (462-08-8) + zinc(II) nitrate hexahydrate + N-tosyl-L-glutamic acid (4816-80-2) → C12H13NO6S(2-)*Zn(2+)*C5H6N2*3H2O

Conditions	Yield
With sodium hydroxide In water at 140℃; for 168h; pH=5;	45%

4-(2-pyridyl)pyridine (581-47-5) + nickel(II) nitrate hexahydrate + N-tosyl-L-glutamic acid (4816-80-2) → Ni((+)-N-p-tolylsulfonylglutamate)(2,4'-bipyridine)2(H2O)2](n)*5nH2O

Conditions	Yield
In water High Pressure; mixing of Ni(NO3)2*6H2O, N-p-tolylsulfonyl-L-glutamic acid and 2,4'-bipyin H2O in Teflon reactor, heating to 120°C for 3 d; slow cooling to room temp., crystn., elem. anal.;	44.9%

1,3,5-Trioxan (110-88-3) + N-tosyl-L-glutamic acid (4816-80-2) → 3-[(4S)-5-oxo-3-(toluene-4-sulfonyl)-oxazolidin-4-yl]-propionic acid (91958-79-1)

Conditions	Yield
With dichloromethane; toluene-4-sulfonic acid; benzene
With thionyl chloride; acetic anhydride; acetic acid

formaldehyd (50-00-0) + N-tosyl-L-glutamic acid (4816-80-2) → 3-[(4S)-5-oxo-3-(toluene-4-sulfonyl)-oxazolidin-4-yl]-propionic acid (91958-79-1)

Conditions	Yield
With thionyl chloride; acetic anhydride; acetic acid
With toluene-4-sulfonic acid at 135℃;

Upstream product

• 56-86-0 L-glutamic acid 
• 98-59-9 p-toluenesulfonyl chloride 
• 55666-46-1 C₂₀H₃₁NO₆S 
• 32677-01-3 L-glutamic acid di-tert-butyl ester hydrochloride 

Downstream Products

• 91958-79-1 3-[(4S)-5-oxo-3-(toluene-4-sulfonyl)-oxazolidin-4-yl]-propionic acid 
• 108590-52-9 2-(4'-methylbenzenesulfonyl)-L-glutamic acid dichloride 
• 21957-65-3 1-(4'-methylbenzenesulfonyl)-5-oxopyrrolidine-2-carboxylic acid 
• 108541-02-2 5-oxo-1-(toluene-4-sulfonyl)-L-prolyl chloride 
• 886203-20-9 acetic acid-[5-oxo-1-(toluene-4-sulfonyl)-L-proline]-anhydride 
• 6970-25-8 1-((4-methylbenzene)sulfonyl)-5-oxopyrrolidine-2-carboxylic acid 
• 95365-68-7 N--L-glutaminsaeure-α-benzylester 
• 95305-51-4 dimethyl (2S)-2-{[(4-methylphenyl)sulfonyl]amino}pentane-1,5-dioate 
• 102017-14-1 N¹-phenyl-N²-(toluene-4-sulfonyl)-L-isoglutamine 
• 56-85-9 L-glutamine 
• 106405-91-8 γ-(4-Nitro-benzyl)-N-tosyl-L-glutaminsaeure 
• 102214-35-7 N--L-glutaminsaeure-α-<4-nitro-benzylester>-γ-benzylester 
• 860644-55-9 (-)-2'-cyclopentyl-2'-phenyl-2'-hydroxyacetic acid [N-(2,2,2-trichloroethoxyformyl)-3-aza-bicyclo[3.3.1]nonan-9-yl]ester (+)-N-p-tosylglutamic acid salt 

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