N-(4-aminobenzoyl)-L-glutamic acid
Conditions | Yield |
---|---|
With ammonium formate; palladium-carbon In methanol | 99% |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; ammonium formate In methanol at 20℃; for 0.5h; Time; Concentration; | 96.58% |
With palladium on carbon; hydrazine hydrate In ethanol at 80℃; for 2.5h; | 78% |
With ethanol; palladium Hydrogenation; |
dimethyl p-trifluoroacetamidobenzoyl-L-glutamate
N-(4-aminobenzoyl)-L-glutamic acid
Conditions | Yield |
---|---|
With sodium hydroxide; water In methanol at 23℃; for 4h; | 61% |
diethyl N-(p-aminobenzoyl)-L-glutamate
N-(4-aminobenzoyl)-L-glutamic acid
(S)-2-(4-(((2-amino-4-hydroxypteridin-6-yl)methyl)amino)benzamido)pentanedioic acid
A
N-(4-aminobenzoyl)-L-glutamic acid
B
4-amino-benzoic acid
C
pterin-6-carboxylic acid
D
6-pterinaldehyde
Conditions | Yield |
---|---|
With hydroxide In water Product distribution; |
(S)-2-(4-(((2-amino-4-hydroxypteridin-6-yl)methyl)amino)benzamido)pentanedioic acid
A
N-(4-aminobenzoyl)-L-glutamic acid
B
pterin-6-carboxylic acid
C
6-pterinaldehyde
Conditions | Yield |
---|---|
With phosphate-buffered saline pH=7.4; UV-irradiation; |
B
N-(4-aminobenzoyl)-L-glutamic acid
Conditions | Yield |
---|---|
In phosphate buffer at 25 - 30℃; pH=7.4; Kinetics; UV-irradiation; |
Conditions | Yield |
---|---|
With oxygen; rose bengal In water-d2 pH=10.5; Kinetics; Irradiation; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 79 percent / SOCl2 / 18 h / Ambient temperature 2: 70 percent / HOBt, DCC, DIEA / tetrahydrofuran / 48 h / -5 °C 3: 61 percent / NaOH, H2O / methanol / 4 h / 23 °C View Scheme | |
Multi-step reaction with 2 steps 1: aq. NaOH solution 2: palladium; ethanol / Hydrogenation View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 70 percent / HOBt, DCC, DIEA / tetrahydrofuran / 48 h / -5 °C 2: 61 percent / NaOH, H2O / methanol / 4 h / 23 °C View Scheme |
2,2,2-trifluoro-N-(4-iodophenyl)acetamide
N-(4-aminobenzoyl)-L-glutamic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) n-BuLi / 1.) ether, hexane, -78 deg C, 2 h, 2.) ether, hexane, -78 deg C to r.t. 2: 70 percent / HOBt, DCC, DIEA / tetrahydrofuran / 48 h / -5 °C 3: 61 percent / NaOH, H2O / methanol / 4 h / 23 °C View Scheme |
L-glutamic dimethyl ester hydrochloride
N-(4-aminobenzoyl)-L-glutamic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 70 percent / HOBt, DCC, DIEA / tetrahydrofuran / 48 h / -5 °C 2: 61 percent / NaOH, H2O / methanol / 4 h / 23 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 78 percent / CH2Cl2 / 1 h / Ambient temperature 2: 1.) n-BuLi / 1.) ether, hexane, -78 deg C, 2 h, 2.) ether, hexane, -78 deg C to r.t. 3: 70 percent / HOBt, DCC, DIEA / tetrahydrofuran / 48 h / -5 °C 4: 61 percent / NaOH, H2O / methanol / 4 h / 23 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous hydrochloric acid 2: palladium; ethanol / Hydrogenation View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: benzene 2: aqueous hydrochloric acid 3: palladium; ethanol / Hydrogenation View Scheme | |
Multi-step reaction with 2 steps 1: benzene; calcium oxide / <40 2: aqueous ammonium sulfide View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide; bis(trichloromethyl) carbonate / 1 h / 40 °C 2: sodium hydroxide / water / 1 h / 0 - 20 °C / pH 8 3: palladium 10% on activated carbon; ammonium formate / methanol / 0.5 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: oxalyl dichloride / tetrahydrofuran; N,N-dimethyl-formamide / 55 °C 2.1: sodium hydroxide / water 2.2: 5 °C / pH 8 3.1: iron(III) chloride hexahydrate; hydrazine hydrate / methanol / 20 °C View Scheme |
Conditions | Yield |
---|---|
In water UV-irradiation; |
Conditions | Yield |
---|---|
With Pt(Py)2(N3)2(OH)2 In dimethylsulfoxide-d6; water-d2 at 37℃; for 2h; Irradiation; |
N-(4-aminobenzoyl)-L-glutamic acid
2-amino-4-hydroxy-6-bromomethylpteridine
(S)-2-(4-(((2-amino-4-hydroxypteridin-6-yl)methyl)amino)benzamido)pentanedioic acid
Conditions | Yield |
---|---|
In N,N-dimethyl acetamide at 45℃; for 4h; Concentration; Temperature; Solvent; Industrial scale; | 89% |
N-(4-aminobenzoyl)-L-glutamic acid
(S)-2-(4-(((2-amino-4-hydroxypteridin-6-yl)methyl)amino)benzamido)pentanedioic acid
Conditions | Yield |
---|---|
In methanol at 45℃; for 5h; Concentration; Temperature; Solvent; Industrial scale; | 85% |
Conditions | Yield |
---|---|
With 1,1,1-trichloroacetone; sodium sulfite In water at 40 - 50℃; for 1h; pH=3 - 4; pH-value; Temperature; | 85% |
1,1,3-trichloroacetone
N-(4-aminobenzoyl)-L-glutamic acid
2,4,5-triamino-6-hydroxypyrimidine sulfate
folate
Conditions | Yield |
---|---|
With sodium metabisulfite at 20 - 30℃; for 2h; Temperature; Ionic liquid; | 83.2% |
With sodium metabisulfite; sodium acetate at 45℃; for 3h; Temperature; | 46.2% |
N-(4-aminobenzoyl)-L-glutamic acid
2-amino-6-(bromomethyl)-4(1H)-pteridinone hydrobromide
folic acid
Conditions | Yield |
---|---|
In N,N-dimethyl acetamide 1.) 22-25 deg C, 96 h; 2.) 50-60 deg C, 30 min; 3.) 22-25 deg C, 24 h; | 80% |
1,1,3-trichloroacetone
N-(4-aminobenzoyl)-L-glutamic acid
2,4,5-triamino-6-hydroxypyrimidine sulfate
(S)-2-(4-(((2-amino-4-hydroxypteridin-6-yl)methyl)amino)benzamido)pentanedioic acid
Conditions | Yield |
---|---|
With sodium hydroxide at 55℃; for 9h; pH=3; | 80% |
Stage #1: 1,1,3-trichloroacetone; 2,4,5-triamino-6-hydroxypyrimidine sulfate With sodium metabisulfite In methanol; water for 0.5h; Large scale; Stage #2: N-(4-aminobenzoyl)-L-glutamic acid With sodium hydroxide In methanol; water at 40 - 45℃; for 6h; pH=3 - 3.5; Solvent; Large scale; | 69.7% |
1,1,1-trichloroacetone
N-(4-aminobenzoyl)-L-glutamic acid
2,4,5-triamino-6-hydroxypyrimidine sulfate
folate
Conditions | Yield |
---|---|
Stage #1: 1,1,1-trichloroacetone; N-(4-aminobenzoyl)-L-glutamic acid With sodium acetate; sodium sulfite In acetic acid at 43℃; for 0.5h; Stage #2: 2,4,5-triamino-6-hydroxypyrimidine sulfate In acetic acid at 38℃; for 5h; | 75.5% |
6-bromomethyl-pteridine-2,4-diamine
N-(4-aminobenzoyl)-L-glutamic acid
aminopterin
Conditions | Yield |
---|---|
In dimethylacetamide (DMAC) at 25℃; for 2h; | 68% |
In ISOPROPYLAMIDE at 25℃; for 18h; | 68% |
N-(4-aminobenzoyl)-L-glutamic acid
water
6-bromomethyl-2,4-diaminopteridine hydrobromide
aminopterin
Conditions | Yield |
---|---|
In ethanol | 68% |
N-(4-aminobenzoyl)-L-glutamic acid
<7-15N>guanide
Conditions | Yield |
---|---|
Stage #1: [3-(13)C]-D-glucose With cysteine disulfide; pyruvate kinase from rabbit muscle; glutaredoxin 2; glucose-6-phosphate dehydrogenase from L. mesenteroides; glutathione reductase from baker’s yeast; hexokinase type F-300 from S. cerevisiae; myokinase from rabbit muscle; phosphoriboisomerase type I from spinach; potassium chloride; NADP; phospho(enol)pyruvic acid mono potassium salt; ATP; magnesium chloride In aq. buffer at 37℃; pH=7; Glovebox; Inert atmosphere; Enzymatic reaction; Stage #2: With guanylate kinase; ribose-phosphate pyrophosphokinase; xanthine guanine phosphoribosyl transferase In aq. buffer for 0.25h; Glovebox; Inert atmosphere; Enzymatic reaction; Stage #3: N-(4-aminobenzoyl)-L-glutamic acid; <7-15N>guanide Further stages; | 30% |
D-Glucose
2-amino-1,9-dihydro-6H-purin-6-one
N-(4-aminobenzoyl)-L-glutamic acid
(S)-2-{4-[(2-Amino-4-oxo-3,4,7,8-tetrahydro-pteridin-6-ylmethyl)-amino]-benzoylamino}-pentanedioic acid
Conditions | Yield |
---|---|
Stage #1: D-Glucose With cysteine disulfide; pyruvate kinase from rabbit muscle; glutaredoxin 2; glucose-6-phosphate dehydrogenase from L. mesenteroides; glutathione reductase from baker’s yeast; hexokinase type F-300 from S. cerevisiae; myokinase from rabbit muscle; phosphoriboisomerase type I from spinach; NADP; phospho(enol)pyruvic acid mono potassium salt; ATP In aq. buffer at 37℃; pH=7; Glovebox; Inert atmosphere; Enzymatic reaction; Stage #2: With guanylate kinase; ribose-phosphate pyrophosphokinase; xanthine guanine phosphoribosyl transferase In aq. buffer for 0.25h; Glovebox; Inert atmosphere; Enzymatic reaction; Stage #3: 2-amino-1,9-dihydro-6H-purin-6-one; N-(4-aminobenzoyl)-L-glutamic acid Further stages; | 30% |
N-(4-aminobenzoyl)-L-glutamic acid
2-amino-O4-benzyl-6-formylpteridine
Conditions | Yield |
---|---|
With sodium cyanoborohydride In N,N-dimethyl-formamide for 0.0833333h; | 17.7% |
Stage #1: N-(4-aminobenzoyl)-L-glutamic acid; 2-amino-O4-benzyl-6-formylpteridine In DMF (N,N-dimethyl-formamide) Stage #2: With sodium cyanoborohydride; acetic acid In DMF (N,N-dimethyl-formamide) for 0.0833333h; | 17.7% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; sodium hydrogensulfite; <1,3-13C2> dichloroacetone In ethanol for 72h; pH 4.0; | 10% |
methanol
N-(4-aminobenzoyl)-L-glutamic acid
dimethyl N-(4-amino-benzoyl)-L-glutamate
Conditions | Yield |
---|---|
With acetyl chloride |
Conditions | Yield |
---|---|
With ethanol |
formic acid
N-(4-aminobenzoyl)-L-glutamic acid
N-(4-formylamino-benzoyl)-L-glutamic acid
4,5,6-triamino-1H-pyrimidine-2-thione
2,3-dibromopropanal
N-(4-aminobenzoyl)-L-glutamic acid
N-{4-[(4-amino-2-thioxo-1,2-dihydro-pteridin-6-ylmethyl)-amino]-benzoyl}-L-glutamic acid
5,6-diaminouracil
2,3-dibromopropanal
N-(4-aminobenzoyl)-L-glutamic acid
N-{4-[(2,4-dioxo-1,2,3,4-tetrahydro-pteridin-6-ylmethyl)-amino]-benzoyl}-L-glutamic acid
Conditions | Yield |
---|---|
With sodium acetate; acetic acid |
5,6-diaminouracil
1,1,3-tribromoacetone
N-(4-aminobenzoyl)-L-glutamic acid
N-{4-[(2,4-dioxo-1,2,3,4-tetrahydro-pteridin-6-ylmethyl)-amino]-benzoyl}-L-glutamic acid
Conditions | Yield |
---|---|
With aqueous solution of pH 1-5 |
2,5,6-triamino-3,4-dihydro-4-pyrimidinone
1,1,3-trichloroacetone
N-(4-aminobenzoyl)-L-glutamic acid
folic acid
2,5,6-triamino-3,4-dihydro-4-pyrimidinone
1,1,3-tribromoacetone
N-(4-aminobenzoyl)-L-glutamic acid
folic acid
2,5,6-triamino-3,4-dihydro-4-pyrimidinone
2,2,3-tribromopropanal
N-(4-aminobenzoyl)-L-glutamic acid
folic acid
2,5,6-triamino-3,4-dihydro-4-pyrimidinone
N-(4-aminobenzoyl)-L-glutamic acid
N-((Ξ)-9-methyl-pteroyl)-L-glutamic acid
Conditions | Yield |
---|---|
With 2,2,3-trichlorobutyraldehyde |
3-phthalimidopropionyl chloride
N-(4-aminobenzoyl)-L-glutamic acid
Conditions | Yield |
---|---|
With 1,4-dioxane; water; magnesium oxide |
The L-Glutamic acid,N-(4-aminobenzoyl)-, with the CAS registry number 4271-30-1, is also known as p-Aminobenzoyl-L-glutamic acid and L-N-(p-Aminobenzoyl)glutamic acid. It belongs to the product categories of Amino Acids; A - Hpeptide Synthesis; Amino Acid Derivatives; Amino Acids; Glutamic Acid and Modified Amino Acids. Its EINECS registry number is 224-261-7. This chemical's molecular formula is C12H14N2O5 and molecular weight is 266.25. What's more, its IUPAC name is 2-[(4-Aminobenzoyl)amino]pentanedioic acid and systematic name is called N-(4-Aminobenzoyl)-L-glutamic acid. This chemical is beige crystalline powder. In addition, it can be used as major metabolite of 5-Methyltetrahydrofolic acid.
Physical properties about L-Glutamic acid,N-(4-aminobenzoyl)- are: (1) ACD/LogP: -0.99; (2) # of Rule of 5 Violations: 1; (3) ACD/BCF (pH 5.5): 1; (4) ACD/BCF (pH 7.4): 1; (5) ACD/KOC (pH 5.5): 1; (6) ACD/KOC (pH 7.4): 1; (7) #H bond acceptors: 7; (8) #H bond donors: 5; (9) #Freely Rotating Bonds: 7; (10) Polar Surface Area: 76.15 Å2; (11) Index of Refraction: 1.617; (12) Molar Refractivity: 65.73 cm3; (13) Molar Volume: 187.7 cm3; (14) Surface Tension: 71.7 dyne/cm; (15) Density: 1.418 g/cm3; (16) Flash Point: 320.9 °C; (17) Enthalpy of Vaporization: 94.87 kJ/mol; (18)Boiling Point: 607.1 °C at 760 mmHg; (19) Vapour Pressure: 1.37E-15 mmHg at 25 °C; (20) Melting Point: 175 °C.
Preparation of L-Glutamic acid,N-(4-aminobenzoyl)-: p-Nitrobenzoyl chloride and Glutamic acid by condensation, then reducing it use Vulcanization ammonium.
Uses of L-Glutamic acid,N-(4-aminobenzoyl)-: (1) it is used as medicinesintermediates; (2) it is used to product Methotrexate and Folic acid.
When you are dealing with this chemical, you should be very careful. This chemical is irritating to eyes, respiratory system and skin. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. And in case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1) SMILES: O=C(c1ccc(N)cc1)N[C@H](C(=O)O)CCC(=O)O
(2) InChI: InChI=1/C12H14N2O5/c13-8-3-1-7(2-4-8)11(17)14-9(12(18)19)5-6-10(15)16/h1-4,9H,5-6,13H2,(H,14,17)(H,15,16)(H,18,19)/t9-/m0/s1
(3) InChIKey: GADGMZDHLQLZRI-VIFPVBQEBD
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