52787-14-1

Basic information

• Product Name: 4-METHOXYCARBONYLMETHYL-BENZOIC ACID METHYL ESTER
• Synonyms: methyl 4-(2-methoxy-2-oxoethyl)benzoate;Methyl 4-methoxycarbonylphenylacetate;Benzeneacetic acid, 4-(Methoxycarbonyl)-,Methyl ester;DiMethyl hoMoterephthalate;4-METHOXYCARBONYLMETHYL-BENZOIC ACID MET...;4-METHOXYCARBONYLMETHYL-BENZOIC ACID METHYL ESTER
• CAS NO: 52787-14-1
• Molecular Formula: C₁₁H₁₂O₄
• Molecular Weight: 208.21
• EINECS: 1806241-263-5
• Product Categories: Intermediate of Pralatrexate
• Mol File: 52787-14-1.mol
• Article Data: 24

Chemical Properties

• Melting Point: 20 °C
• Boiling Point: 122°C/0.6mmHg(lit.)
• Flash Point: 145.419 °C
• Appearance: /
• Density: 1.155
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.511
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 4-METHOXYCARBONYLMETHYL-BENZOIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXYCARBONYLMETHYL-BENZOIC ACID METHYL ESTER(52787-14-1)
• EPA Substance Registry System: 4-METHOXYCARBONYLMETHYL-BENZOIC ACID METHYL ESTER(52787-14-1)

Safety Data

• Hazardous Substances Data: 52787-14-1(Hazardous Substances Data)

Usage

Uses

4-Methoxycarbonylmethyl-benzoic acid methyl ester is an intermediate for the preparation of 10-Propargyl-10-deazaaminopterin with anti tumor activity.

InChI:InChI=1/C11H12O4/c1-14-10(12)7-8-3-5-9(6-4-8)11(13)15-2/h3-6H,7H2,1-2H3

Synthetic route

methanol (67-56-1) + 4-(carboxymethyl)benzoic acid (501-89-3) → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1)

Conditions	Yield
With thionyl chloride In N,N-dimethyl-formamide at 50℃; for 4h;	95%
With sulfuric acid at 90℃; for 19h;	93%
With sulfuric acid a) from 20 deg C to 25 deg C, 3 d, b) reflux, 4.5 h;	91%

methanol (67-56-1) + 1,1-dibromo-2-(4-methoxycarbonylphenyl)ethene (253684-21-8) → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1)

Conditions	Yield
With triethylsilane; cyclohexa-1,4-diene; oxygen; cobalt acetylacetonate In nonane at 24℃; under 760.051 Torr; Reagent/catalyst;	92%

methanol (67-56-1) + 4-(carboxymethyl)benzoic acid (501-89-3) → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + 4-(methoxycarbonylmethyl)benzoic acid (87524-66-1)

Conditions	Yield
With thionyl chloride at 25 - 27℃; for 7h; Esterification;	A 5% B 90%
With nickel dichloride for 10h; Heating;	A 6% B 85%
With phosphorus pentoxide; copper(II) sulfate; sodium sulfate for 4h; Heating;	A 20% B 70%

methanol (67-56-1) + 4-ethynylbenzoic acid methyl ester (3034-86-4) → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1)

Conditions	Yield
With 4-methylpyridine-1-oxide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; P(p-C6H4F)3 In acetonitrile at 60℃; for 2h; chemoselective reaction;	83%

methanol (67-56-1) + methyl 4-(cyanomethyl)benzoate (76469-88-0) → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1)

Conditions	Yield
With hydrogenchloride for 2h; Reflux;	81%
With hydrogenchloride at 20℃; for 32h; Heating / reflux;

4-methoxycarbonylphenyl bromide (619-42-1) + methyl chloroacetate (96-34-4) → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1)

Conditions	Yield
With manganese; (2,2'-bipyridine)nickel(II) dibromide; trifluoroacetic acid In N,N-dimethyl-formamide at 50℃; for 1h;	72%

methanol (67-56-1) + 4-Trifluoromethylphenylacetic acid (32857-62-8) → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1)

Conditions	Yield
Stage #1: 4-Trifluoromethylphenylacetic acid With sodium hydride In acetonitrile for 20h; Heating; Stage #2: methanol; sulfuric acid for 2h; Heating;	51%

nickel (II) chloride hexahydrate + 4-(carboxymethyl)benzoic acid (501-89-3) → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1)

Conditions	Yield
In methanol	28.8%
In methanol	28.8%

4-Bromophenylacetonitrile (16532-79-9) + carbon monoxide (201230-82-2) + sodium methylate (124-41-4) → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + (4-bromo-phenyl)-acetic acid methyl ester (41841-16-1) + methyl 4-(cyanomethyl)benzoate (76469-88-0)

Conditions	Yield
With dicobalt octacarbonyl In methanol at 50℃; Product distribution; Mechanism; Irradiation; other p-halogenobenzyl cyanides, var. time and initial concn.;

triptycene (477-75-8) + acetyl chloride (75-36-5) → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + 2,6-diacetyltriptycene (140245-70-1) + 2,7-diacetyltriptycene (140245-69-8) + C26H20O3

Conditions	Yield
With hydrogenchloride; aluminium trichloride In nitromethane; dichloromethane for 1.66667h; Further byproducts given. Title compound not separated from byproducts;

4-methoxycarbonimidoylmethyl-benzoic acid methyl ester; hydrochloride → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1)

Conditions	Yield
With sodium hydrogencarbonate In diethyl ether Yield given;

4-methyl-benzoic acid methyl ester (99-75-2) + CO2 anion radical → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 80 percent / N-bromosuccinimide, dibenzoyl-peroxide / CCl4 / 2.5 h / Heating 2: 54 percent / dimethylsulfoxide / 2 h / 40 °C 3: HCl / 8 h / Heating 4: aq. NaHCO3 / diethyl ether View Scheme

Methyl 4-(bromomethyl)benzoate (2417-72-3) → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 54 percent / dimethylsulfoxide / 2 h / 40 °C 2: HCl / 8 h / Heating 3: aq. NaHCO3 / diethyl ether View Scheme
Multi-step reaction with 3 steps 1: water; methanol / 5 h / Reflux 2: sodium hydroxide / methanol / 90 °C 3: sulfuric acid / 90 °C View Scheme
Multi-step reaction with 3 steps 1: tetrabutyl ammonium fluoride / acetonitrile / 12 h / 25 °C 2: sodium hydroxide; water / methanol / 12 h / 90 °C 3: sulfuric acid / 18 h / 90 °C View Scheme

methyl 4-(cyanomethyl)benzoate (76469-88-0) → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / 8 h / Heating 2: aq. NaHCO3 / diethyl ether View Scheme
With hydrogenchloride In methanol at 20℃; for 32h; Heating / reflux;
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol / 90 °C 2: sulfuric acid / 90 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide; water / methanol / 12 h / 90 °C 2: sulfuric acid / 18 h / 90 °C View Scheme

p-(chloromethyl)benzoic acid (1642-81-5) → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 100 percent / aq. NaHCO3 / tetrahydrofuran / 48 h / 20 - 25 °C 2: 90 percent / aq. H2SO4 / 6 h / Heating 3: 91 percent / H2SO4 / a) from 20 deg C to 25 deg C, 3 d, b) reflux, 4.5 h View Scheme

4-(cyanomethyl)benzoic acid (50685-26-2) → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / aq. H2SO4 / 6 h / Heating 2: 91 percent / H2SO4 / a) from 20 deg C to 25 deg C, 3 d, b) reflux, 4.5 h View Scheme

(4-isopropylphenyl)acetonitrile (4395-87-3) → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous nitric acid 2: sulfuric acid View Scheme

4-(cyanomethyl)benzonitrile (876-31-3) → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous sulfuric acid 2: sulfuric acid View Scheme

1,3-bis-(diphenylphosphino)propane (6737-42-4) + (4-Trifluoromethanesulfonyloxy-phenyl)-acetic acid methyl ester (147283-85-0) → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1)

Conditions	Yield
bis(triphenylphosphine)palladium(II)-chloride In methanol; dimethyl sulfoxide

Ethyl 2-phenylethanoate (101-97-3) → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / carbon disulfide / 12 h / 50 °C 2.1: sodium hydroxide / tetrahydrofuran; water / 1.5 h / 20 °C 3.1: potassium hydroxide / water; 1,4-dioxane / 0.17 h / 0 °C / Cooling with ice 3.2: 3 h / 0 °C / Cooling with ice 4.1: thionyl chloride / N,N-dimethyl-formamide / 4 h / 50 °C View Scheme

ethyl 4-acetylphenylacetate (1528-42-3) → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / tetrahydrofuran; water / 1.5 h / 20 °C 2.1: potassium hydroxide / water; 1,4-dioxane / 0.17 h / 0 °C / Cooling with ice 2.2: 3 h / 0 °C / Cooling with ice 3.1: thionyl chloride / N,N-dimethyl-formamide / 4 h / 50 °C View Scheme

sodium 4-acetyl-phenylacetate → methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium hydroxide / water; 1,4-dioxane / 0.17 h / 0 °C / Cooling with ice 1.2: 3 h / 0 °C / Cooling with ice 2.1: thionyl chloride / N,N-dimethyl-formamide / 4 h / 50 °C View Scheme

methyl coumalate (6018-41-3) + Methyl 3,3-dimethoxy-2-methylbutanoate → dimethyl 4-methylbenzene-1,3-dicarboxylate (23038-61-1) + methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1)

Conditions	Yield
In toluene at 200℃; for 16h; Overall yield = 76 %; regioselective reaction;

methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) → [4-(methoxycarbonyl)phenyl]acetic acid (22744-12-3)

Conditions	Yield
With lithium hydroxide monohydrate; water In tetrahydrofuran; ethanol at 25℃; for 10h;	94.4%
With water; potassium carbonate In methanol at 20℃; for 24h;	93%
With potassium carbonate In water 100 deg C, 5 min; 35 deg C, 1 h;	85%

methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) → 1-(hydroxymethyl)-4-(2-hydroxyethyl)benzene (4866-85-7)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 20 - 30℃; Cooling with ice;	90%
With lithium aluminium tetrahydride In diethyl ether Reflux;	89%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2h;

methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + allyl bromide (106-95-6) → 4-(1-Methoxycarbonyl-but-3-enyl)-benzoic acid methyl ester (153802-44-9)

Conditions	Yield
With potassium hydride	89%

methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + propargyl bromide (106-96-7) → α-propargylhomoterephthalic acid dimethyl ester (146464-90-6)

Conditions	Yield
Stage #1: methyl 4-(2-methoxy-2-oxoethyl)benzoate; propargyl bromide In tetrahydrofuran at -10℃; Inert atmosphere; Stage #2: With lithium hexamethyldisilazane In tetrahydrofuran at -10℃; Temperature; Solvent; Reagent/catalyst;	87%
Stage #1: methyl 4-(2-methoxy-2-oxoethyl)benzoate With sodium hydride In tetrahydrofuran at 0 - 15℃; Autoclave; Stage #2: propargyl bromide In tetrahydrofuran at -20 - 10℃; for 5h;	64.5%
With potassium hydride 1.) THF, 0 deg C, 1 h, 2.) THF, a0) o deg C, 30 min, b) RT, 16 h; Yield given. Multistep reaction;

methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) → 1-(2-hydroxyethyl)-4-(3-hydroxypropyl)benzene (143260-83-7)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether Reflux;	85%

methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + trimethyl((1-phenylcyclopentyl)peroxy)silane → methyl 4-(1-methoxy-1,7-dioxo-7-phenylheptan-2-yl)benzoate

Conditions	Yield
Stage #1: methyl 4-(2-methoxy-2-oxoethyl)benzoate With dmap; copper(l) iodide In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: trimethyl((1-phenylcyclopentyl)peroxy)silane In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	80%

methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + 4-(Diethylamino)salicylaldehyde (17754-90-4) → 4-(7-Diethylamino-2-oxo-2H-chromen-3-yl)-benzoic acid methyl ester (177093-56-0)

Conditions	Yield
With piperidine; pyridine at 100℃; for 15h;	76%

methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + aniline (62-53-3) → methyl 4-(2-oxo-2-(phenylamino)ethyl)benzoate (1276030-38-6)

Conditions	Yield
With C18H15IMnN3O3; sodium t-butanolate In toluene at 90℃; for 18h; Inert atmosphere; Schlenk technique;	76%
With bis(1,5-cyclooctadiene)nickel (0); C45H61N2(1+)*Cl(1-); potassium tert-butylate In toluene at 140℃; for 16h; Reagent/catalyst;	65%

methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + trimethyl((1-phenylcycloheptyl)peroxy)silane → methyl 4-(1-methoxy-1,9-dioxo-9-phenylnonan-2-yl)benzoate

Conditions	Yield
Stage #1: methyl 4-(2-methoxy-2-oxoethyl)benzoate With dmap; copper(l) iodide In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: trimethyl((1-phenylcycloheptyl)peroxy)silane In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	75%

methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + trimethyl((1-(p-tolyl)cyclopentyl)peroxy)silane → methyl 4-(1-methoxy-1,7-dioxo-7-(4-tolyl)heptan-2-yl)benzoate

Conditions	Yield
Stage #1: methyl 4-(2-methoxy-2-oxoethyl)benzoate With dmap; copper(l) iodide In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: trimethyl((1-(p-tolyl)cyclopentyl)peroxy)silane In N,N-dimethyl-formamide at 50℃; for 1h; Inert atmosphere;	73%

(2-nitroethenyl)benzene (102-96-5) + methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) → C19H19NO6

Conditions	Yield
Stage #1: methyl 4-(2-methoxy-2-oxoethyl)benzoate With 1-((1R,2R)-2-aminocyclohexyl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Michael Addition; Stage #2: (2-nitroethenyl)benzene In N,N-dimethyl-formamide at 20℃; for 48h; Michael Addition; diastereoselective reaction;	70%

methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + aniline (62-53-3) → methyl 4-(2-oxo-2-(phenylamino)ethyl)benzoate (1276030-38-6) + 4-(2-oxo-2-(phenylamino)ethyl)-N-phenylbenzamide

Conditions	Yield
With C18H15IMnN3O3; sodium t-butanolate In toluene at 120℃; for 18h; Catalytic behavior; Temperature; Inert atmosphere; Schlenk technique;	A 66% B 28%

cyclopentylmethyl Iodide (27935-87-1) + methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + ammonium chloride → 4-(2-cyclopentyl-1-methoxycarbonyl-ethyl)-benzoic acid methyl ester

Conditions	Yield
In tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone	65.7%
In tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone	65.7%

methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + propargyl bromide (106-96-7) → dipropargyl homoterephthalic acid dimethyl ester (1026380-17-5) + α-propargylhomoterephthalic acid dimethyl ester (146464-90-6)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl acetamide at 25 - 30℃; for 26h; Concentration;	A n/a B 65.6%
Stage #1: methyl 4-(2-methoxy-2-oxoethyl)benzoate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Stage #2: propargyl bromide In tetrahydrofuran; mineral oil at 0 - 20℃; for 17h;
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl acetamide at 25 - 30℃; Concentration;

methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → methyl 4-(1-(dimethylamino)-3-methoxy-3-oxoprop-1-en-2-yl)benzoate

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 4h;	63%

methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + 1,4-dibenzoyloxy-9,10-anthraquinone (33266-08-9) → C34H20O8

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 100℃; for 1h; Inert atmosphere;	58%

methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + methyl iodide (74-88-4) → 4-(1-methoxycarbonyl-ethyl)-benzoic acid methyl ester (77959-48-9)

Conditions	Yield
Stage #1: methyl 4-(2-methoxy-2-oxoethyl)benzoate With sodium hydride In tetrahydrofuran at 0℃; for 1h; Metallation; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; for 16.5h; Methylation; Further stages.;	56%
With potassium hydride 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C, 30 min; Yield given. Multistep reaction;

methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + trimethyl((1-phenylcyclohexyl)peroxy)silane → methyl 4-(1-methoxy-1,8-dioxo-8-phenyloctan-2-yl)benzoate

Conditions	Yield
Stage #1: methyl 4-(2-methoxy-2-oxoethyl)benzoate With dmap; copper(l) iodide In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: trimethyl((1-phenylcyclohexyl)peroxy)silane In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	56%

methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + C20H34O2Si → methyl 4-(1-cyclohexyl-2-methoxy-2-oxoethyl)benzoate

Conditions	Yield
Stage #1: methyl 4-(2-methoxy-2-oxoethyl)benzoate With dmap; copper(l) iodide In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: C20H34O2Si In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	55%

methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + (E)-benzalacetone (1896-62-4) → C21H22O5 (1300627-45-5)

Conditions	Yield
With pyrrolidine In dichloromethane at 20℃; for 48h; Michael addition;	54%

methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + ethyl iodide (75-03-6) → dimethyl α-ethylhomoterephthalate (88392-91-0)

Conditions	Yield
Stage #1: methyl 4-(2-methoxy-2-oxoethyl)benzoate With sodium hydride In tetrahydrofuran at 0℃; for 1h; Metallation; Stage #2: ethyl iodide In tetrahydrofuran at 0 - 20℃; for 17h; Alkylation; Further stages.;	51%

methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + ((1-(4-fluorophenyl)cyclopentyl)peroxy)trimethylsilane → methyl 4-(7-(4-fluorophenyl)-1-methoxy-1,7-dioxoheptan-2-yl)benzoate

Conditions	Yield
Stage #1: methyl 4-(2-methoxy-2-oxoethyl)benzoate With dmap; copper(l) iodide In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: ((1-(4-fluorophenyl)cyclopentyl)peroxy)trimethylsilane In N,N-dimethyl-formamide at 50℃; for 1h; Inert atmosphere;	50%

methyl 4-(2-methoxy-2-oxoethyl)benzoate (52787-14-1) + 6-bromomethyl-2,4-diaminopteridine hydrobromide (52853-40-4) + propargyl bromide (106-96-7) → methyl-4-(2-((2,4-diaminopteridin-6-yl)methyl)-1-methoxy-1-oxopent-4-yn-2-yl)benzoate (146464-91-7) + 4-[2-(2,4-diamino-pteridin-6-yl)-1-methoxycarbonyl-ethyl]-benzoic acid methyl ester

Conditions	Yield
Multistep reaction;	A n/a B 45%

Upstream product

• 99-75-2 4-methyl-benzoic acid methyl ester 
• 6018-41-3 methyl coumalate 
• 67-56-1 methanol 
• 253684-21-8 1,1-dibromo-2-(4-methoxycarbonylphenyl)ethene 
• 1528-42-3 ethyl 4-acetylphenylacetate 
• 101-97-3 Ethyl 2-phenylethanoate 
• 3034-86-4 4-ethynylbenzoic acid methyl ester 
• 76469-88-0 methyl 4-(cyanomethyl)benzoate 
• 6737-42-4 1,3-bis-(diphenylphosphino)propane 
• 147283-85-0 (4-Trifluoromethanesulfonyloxy-phenyl)-acetic acid methyl ester 
• 501-89-3 4-(carboxymethyl)benzoic acid 
• 876-31-3 4-(cyanomethyl)benzonitrile 
• 4395-87-3 (4-isopropylphenyl)acetonitrile 
• 50685-26-2 4-(cyanomethyl)benzoic acid 

Downstream Products

• 88392-93-2 dimethyl 4-amino-4-deoxy-10-carboxy-8,10-dideazapteroate 
• 106200-45-7 4-amino-4-deoxy-5,10-dideazapteroic acid 
• 106200-47-9 methyl 4-amino-4-deoxy-10-carbomethoxy-5,10-dideazapteroate 
• 106200-48-0 4-{2-[2-Amino-4-(dimethylamino-methyleneamino)-pyrido[2,3-d]pyrimidin-6-yl]-1-methoxycarbonyl-ethyl}-benzoic acid methyl ester 
• 146464-93-9 4-(1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl)benzoic acid 
• 146464-92-8 4-(2-carboxy-1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl)benzoic acid 
• 1324054-53-6 methyl 4-(2-(2,4-dihydroxyphenyl)-2-oxoethyl)benzoate 
• 146464-90-6 α-propargylhomoterephthalic acid dimethyl ester 

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The present invention belongs to the technical field of chemical pharmaceuticals, and relates to a compound represented by general formula (I) or formula (II) and a preparation method thereof. The compounds are biaryl derivatives with RORγt activation activity. The biaryl derivatives disclosed in this invention can effectively activate the RORγt protein receptor, and thereby promote the differentiation of Th17 cells and increasing the production of IL-17, which can be used as an immune modulator for the treatment of various cancers or viral infection-related diseases.

A suitable industrial production pula Qu Sha method for the preparation of

The invention relates to the field of pharmaceutical chemistry technology, and more specifically relates to an anticarcinogen 10-Propargyl-10-deazaaminopterin (Pralatrexate) and synthesis of an intermediate thereof. The invention has the advantages of simple operation, low contents of related impurities, easiness in purification of intermediate, thereby avoiding purification mode of column chromatography, and the invention can be applied to large scale production of Pralatrexate bulk drug as well as preparation and purification method of important intermediates.