627-91-8

Basic information

• Product Name: Monomethyl adipate
• Synonyms: Hexanedioic acid hydrogen 1-methyl;Adipic acid monometh;MonoMethyl adipate, 98% 5GR;Adipic Acid Monomethyl Ester Methyl Hydrogen Adipate Monomethyl Hexanedioate Hexanedioic Acid Monomethyl Ester;Hexanedioic acid,1-Methyl ester;Mono-Methyl adipate 99%;6-Methoxy-6-oxohexanoic acid;Methyl 5-carboxypentanoate
• CAS NO: 627-91-8
• Molecular Formula: C₇H₁₂O₄
• Molecular Weight: 160.17
• EINECS: 211-019-0
• Product Categories: Building Blocks;C6 to C7;Carbonyl Compounds;Chemical Synthesis;Esters;Organic Building Blocks;Senior lubricating oil
• Mol File: 627-91-8.mol
• Article Data: 50

Chemical Properties

• Melting Point: 7-9 °C(lit.)
• Boiling Point: 162 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless/Liquid
• Density: 1.081 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000479mmHg at 25°C
• Refractive Index: n20/D 1.441(lit.)
• Storage Temp.: 2-8°C
• PKA: 4.69±0.10(Predicted)
• Water Solubility: Not miscible or difficult to mix with water.
• BRN: 1766411
• CAS DataBase Reference: Monomethyl adipate(CAS DataBase Reference)
• NIST Chemistry Reference: Monomethyl adipate(627-91-8)
• EPA Substance Registry System: Monomethyl adipate(627-91-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 627-91-8(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

Methyl hydrogen adipate is a useful synthetic intermediate. It can be used to prepare 1,3,4-thiadiazole hydroxamic acid derivatives as novel histone deacetylase inhibitors which show potential antitumor activities. It can be also used to synthesize mannose-linked biphenylylacetic acid derivatives as novel inhibitors of selectin-mediated cell adhesion.

Definition

ChEBI: Monomethyl adipate is a dicarboxylic acid monoester that is the monomethyl ester of adipic acid. It has a role as a metabolite and a plasticiser.

Synthesis

According to the general procedure described above, a has been synthesized from adipic acid (730mg, 5 mmol) and methanol (10 ml). Yield: 80%.The synthetic method of Monomethyl adipate mainly contains following three kinds:The one, under alkaline condition or issue the first portion hydrolysis reaction in the catalysis of bioactive enzyme (pork liver lipase etc.) and obtain Monomethyl adipate (such as document Blaise; Koehler; Bulletin de la Societe Chimique deFrance; Vol. (4) 7; (1910); P.219).The 2nd, by hexanodioic acid or adipic anhydride and ethanol, as catalyzer, the control reaction conditions carries out esterification and obtains Monomethyl adipate (such as document Chem.Zentralbl. with acid; Vol.97; (1926; P.126));The 3rd, by the people such as Swann nineteen forty-three with hexanodioic acid, diethylene adipate and ethanol with the condition of acid as catalyst under control reaction conditions obtain monomethyl adipate(document such as Swann; Oehler; Buswell; Org.synth.Coll.Vol.11; (1943); P.227).Synthetic method of monomethyl adipatehttp://www.orgsyn.org/demo.aspx?prep=CV2P0264

InChI:InChI=1/C7H12O4/c1-11-7(10)5-3-2-4-6(8)9/h2-5H2,1H3,(H,8,9)/p-1

Synthetic route

2-Carboxy-hexanedioic acid 6-methyl ester (81158-34-1) → adipic acid monomethyl ester (627-91-8)

Conditions	Yield
at 160 - 165℃;	100%

hexanedioic acid dimethyl ester (627-93-0) → adipic acid monomethyl ester (627-91-8)

Conditions	Yield
With porcine liver esterase; sodium hydroxide; phosphate buffer for 6h;	96%
With sodium hydroxide; phosphate buffer for 1h; Ambient temperature; pig liver esterase;	84%
With potassium hydroxide In methanol; diethyl ether; acetonitrile at 0℃; for 54h;	71%

methanol (67-56-1) + Adipic acid (124-04-9) → adipic acid monomethyl ester (627-91-8)

Conditions	Yield
With sulfonated poly-divinylbenzene-co-triallylamine at 24.84℃; for 10h;	95%
With acid	32%
With hydrogenchloride Heating;
With hydrogenchloride In water; toluene at 25 - 85℃; for 8.75h;	109.6 g

methyl 6-oxohexanoate (6654-36-0) → adipic acid monomethyl ester (627-91-8)

Conditions	Yield
	95%
With Jones reagent In acetone at 0℃; for 1h; Inert atmosphere;	80%
With Iron(III) nitrate nonahydrate; oxygen In acetonitrile at 25℃; under 760.051 Torr; for 12h; Schlenk technique;	65%

C7H16O3 → adipic acid monomethyl ester (627-91-8)

Conditions	Yield
With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 25℃; for 12h;	94%

methanol (67-56-1) + Adipic acid (124-04-9) → hexanedioic acid dimethyl ester (627-93-0) + adipic acid monomethyl ester (627-91-8)

Conditions	Yield
With nickel dichloride for 13h; Heating;	A 81% B 18%
With aluminum oxide at 25℃; for 48h; Reagent/catalyst; Temperature; Time; Green chemistry; chemoselective reaction;	A 9% B 80%
With carbonic acid dimethyl ester at 180℃; under 10343.2 Torr; for 5h; Solvent; Inert atmosphere;	A 40% B 60%

3-iodopropanoic acid (141-76-4) + acrylic acid methyl ester (292638-85-8) → adipic acid monomethyl ester (627-91-8)

Conditions	Yield
With sodium tetrahydroborate; azobisisobutyronitrile; tributyltin chloride; sodium fluoride Mechanism; 1) EtOH, 20 deg C, 4 h, 2) H2O; other electrophilic olefins;	76%
With sodium tetrahydroborate; azobisisobutyronitrile; tributyltin chloride; sodium fluoride 1) EtOH, r.t., 4 h, 2) H2O; Yield given. Multistep reaction;

O-methylcaprolactim (2525-16-8) + Adipic acid (124-04-9) → caprolactam (105-60-2) + adipic acid monomethyl ester (627-91-8)

Conditions	Yield
at 80 - 85℃; for 16h;	A n/a B 72%

methyl 6-hydroxycaproate (4547-43-7) → adipic acid monomethyl ester (627-91-8)

Conditions	Yield
With chromium(VI) oxide; sulfuric acid In water; acetone for 0.666667h; Ambient temperature;	46%

hexanedioic acid dimethyl ester (627-93-0) + ethanol (64-17-5) → adipic acid monomethyl ester (627-91-8) + diethyl adipate (141-28-6) + adipic acid ethyl methyl ester (18891-13-9)

Conditions	Yield
With water; hydrogen In methanol under 37503.8 Torr;	A 11.2% B 43.5% C 40.5%

hexanedioic acid dimethyl ester (627-93-0) → 6-Hydroxyhexanoic acid (1191-25-9) + adipic acid monomethyl ester (627-91-8) + adipic anhydride (2035-75-8)

Conditions	Yield
With hydrogen In 1,4-dioxane under 37503.8 Torr;	A 34.1% B 42.3% C 21%

2-hydroxy-2-cyclohexen-1-one (10316-66-2) → 1,5-pentanedioic acid (110-94-1) + 5-oxopentanoic acid (5746-02-1) + adipic acid monomethyl ester (627-91-8) + 5,5-dimethoxy-1-oxopentanoic acid (6719-33-1) + methyl 5-carboxy-2-hydroxypentanoate (86544-11-8)

Conditions	Yield
With oxygen; methylene blue In methanol at 30℃; for 10h; Product distribution; Irradiation; yield depends on the reaction conditions (temp., sensitizer, solvent);	A 7% B 9% C 1% D 23% E 33%

methanol (67-56-1) + 2-hydroxy-2-cyclohexen-1-one (10316-66-2) → 1,5-pentanedioic acid (110-94-1) + 5-oxopentanoic acid (5746-02-1) + adipic acid monomethyl ester (627-91-8)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; oxygen; rose bengal at 40℃; for 13h; Irradiation;	A 1% B 5% C 27%

Adipic acid (124-04-9) + hexanedioic acid dimethyl ester (627-93-0) → adipic acid monomethyl ester (627-91-8)

Conditions	Yield
at 230℃;
for 24h; Heating;	35.3 g
In methanol; water
at 160℃; for 24h;

hexanedioic acid dimethyl ester (627-93-0) → adipic acid monomethyl ester (627-91-8) + methyl 2-oxocyclopentane-1-carboxylate (10472-24-9)

Conditions	Yield
With sodium; toluene

diazomethane (186581-53-3, 908094-01-9) + Adipic acid (124-04-9) → adipic acid monomethyl ester (627-91-8)

Conditions	Yield
With aluminum oxide In cyclohexane; N,N-dimethyl-formamide Product distribution; study of selectivity of methylation on alumina surface;

C21H38N4NiO2 + acrylic acid methyl ester (292638-85-8) → adipic acid monomethyl ester (627-91-8)

Conditions	Yield
In tetrahydrofuran at 60℃; for 30h;

Adipic acid (124-04-9) + dimethyl sulfate (77-78-1) → hexanedioic acid dimethyl ester (627-93-0) + adipic acid monomethyl ester (627-91-8)

Conditions	Yield
aluminum oxide In cyclohexane for 2h; Heating; Yield given. Yields of byproduct given;

Adipic acid (124-04-9) + dimethyl sulfate (77-78-1) → adipic acid monomethyl ester (627-91-8) + Monomethyl phthalate (4376-18-5)

Conditions	Yield
aluminum oxide In cyclohexane for 2h; Heating; Yield given. Yields of byproduct given;

methyl 6-oxohexanoate (6654-36-0) → methyl hydrogen succinate (3878-55-5) + Pentanedioic acid, monomethyl ester (1501-27-5) + adipic acid monomethyl ester (627-91-8)

Conditions	Yield
With oxygen; H5PV2Mo10O40(1,11) In acetic acid at 60℃; under 750.06 Torr; Yield given. Yields of byproduct given;

methanol (67-56-1) + 2-nitrocyclohexanone (4883-67-4) → adipic acid monomethyl ester (627-91-8)

Conditions	Yield
With Oxone; potassium hydroxide; sodium hydroxide; disodium hydrogenphosphate; water 1.) 65 deg C, 4 h, 2.) r.t., 4 h; Yield given. Multistep reaction;

Diesel fuel → icosane (112-95-8) + hepatdecane (629-78-7) + n-nonadecane (629-92-5) + adipic acid monomethyl ester (627-91-8)

Conditions	Yield
With air at 1130℃; under 18001.4 Torr; Formation of xenobiotics; high pressure combustion; Further byproducts given. Title compound not separated from byproducts;

biodiesel fuel → Methyl linoleate (112-63-0) + Tridecane (629-50-5) + adipic acid monomethyl ester (627-91-8) + methyl ester of azelaic acid aldehyde (1931-63-1)

Conditions	Yield
With air at 1130℃; under 18001.4 Torr; Formation of xenobiotics; high pressure combustion; Further byproducts given. Title compound not separated from byproducts;

adipic acid (4,5-dimethoxy-2-nitrobenzyl) ester methyl ester (457612-25-8) → adipic acid monomethyl ester (627-91-8)

Conditions	Yield
In acetonitrile for 24h; Irradiation; 419 nm irradiation;	85 % Spectr.
In acetonitrile for 24h; visible light irradiation;

adipic acid (3',5'-dimethoxybenzoin) ester methyl ester (457612-26-9) → adipic acid monomethyl ester (627-91-8)

Conditions	Yield
In acetonitrile for 0.166667h; Irradiation; 254 nm irradiation;	95 % Spectr.
In acetonitrile for 0.0833333h; visible light irradiation;

2-methoxycyclohexanol (2979-24-0) → adipic acid monomethyl ester (627-91-8)

Conditions	Yield
With dihydrogen peroxide; Na12[WZn3(H2O)2(ZnW9O34)2] at 75℃; for 7h;

adipic acid mono(4,5-dimethoxy-2-nitrobenzyl) ester (457612-06-5) → adipic acid monomethyl ester (627-91-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 4.9 mg / benzene; ethanol; hexane / 1 h 2: 85 percent Spectr. / acetonitrile / 24 h / Irradiation; 419 nm irradiation View Scheme
Multi-step reaction with 4 steps 1: 76 percent / 4-(N,N-dimethylamino)pyridine; N,N'-dicyclohexylcarbodiimide / CHCl3 / 24 h / 60 °C 2: 87 percent Spectr. / acetonitrile / 24 h / Irradiation; 419 nm irradiation 3: 5.6 mg / benzene; ethanol; hexane / 1 h 4: 95 percent Spectr. / acetonitrile / 0.17 h / Irradiation; 254 nm irradiation View Scheme

hexanedioic acid mono-[1-(3,5-dimethoxy-phenyl)-2-oxo-2-phenyl-ethyl] ester → adipic acid monomethyl ester (627-91-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 5.6 mg / benzene; ethanol; hexane / 1 h 2: 95 percent Spectr. / acetonitrile / 0.17 h / Irradiation; 254 nm irradiation View Scheme

adipic acid (4,5-dimethoxy-2-nitrobenzyl) ester (3',5'-dimethoxybenzoin) ester (457612-13-4) → adipic acid monomethyl ester (627-91-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 78 percent Spectr. / acetonitrile / 0.17 h / Irradiation; 254 nm irradiation 2: 4.9 mg / benzene; ethanol; hexane / 1 h 3: 85 percent Spectr. / acetonitrile / 24 h / Irradiation; 419 nm irradiation View Scheme
Multi-step reaction with 3 steps 1: 87 percent Spectr. / acetonitrile / 24 h / Irradiation; 419 nm irradiation 2: 5.6 mg / benzene; ethanol; hexane / 1 h 3: 95 percent Spectr. / acetonitrile / 0.17 h / Irradiation; 254 nm irradiation View Scheme

adipic acid monomethyl ester (627-91-8) → methyl adipoyl chloride (35444-44-1)

Conditions	Yield
With phosphorus pentachloride In diethyl ether Ambient temperature;	100%
With thionyl chloride In benzene	100%
With oxalyl dichloride for 2h; Heating;	94%

adipic acid monomethyl ester (627-91-8) + N2-[2R-isobutyl-3S-(9-fluorenylmethoxycarbonylamino)-4-hydroxysuccinyl]-L-tert-leucine-N1-methylamide (204126-54-5) → 5-[(1S,2R)-2-((S)-2,2-Dimethyl-1-methylcarbamoyl-propylcarbamoyl)-1-hydroxycarbamoyl-4-methyl-pentylcarbamoyl]-pentanoic acid methyl ester

Conditions	Yield
Multistep reaction;	100%

adipic acid monomethyl ester (627-91-8) + C40H41NO12 (495390-57-3) → C47H51NO15 (495390-58-4)

Conditions	Yield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In ethanol for 3h; Heating;	100%

adipic acid monomethyl ester (627-91-8) + tert-butyl (2S)-2-[[(2S)-2-aminopropanoyl]amino]propanoate (2488-26-8) → C17H30N2O6

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

adipic acid monomethyl ester (627-91-8) + N(ε)-benzoyloxycarbonyl-L-lysine tert-butyl ester hydrochloride (5978-22-3) → CH3O-Adip-Lys(Z)-OBu-t (93489-31-7)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran 1 h, 0 deg C => 6 h, r.t.;	99%

biphenyl-2-ylcarbamic acid 1-[2-(methylamino)ethyl]piperidin-4-yl ester (743460-48-2) + adipic acid monomethyl ester (627-91-8) → 5-({2-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]ethyl}methylcarbamoyl)pentanoic Acid Methyl Ester (864765-59-3)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide for 15h;	98%

Trimethyl orthoacetate (1445-45-0) + adipic acid monomethyl ester (627-91-8) → hexanedioic acid dimethyl ester (627-93-0)

Conditions	Yield
microwave irradiation;	96%

adipic acid monomethyl ester (627-91-8) + phenol (108-95-2) → C13H16O4

Conditions	Yield
With magnesium hydroxide; lithium hydroxide monohydrate; di-tert-butyl dicarbonate at 25℃; for 24h; Time;	96%

adipic acid monomethyl ester (627-91-8) + bis(2-tert-butyloxycarbonylaminoethyl)amine (117499-16-8) → methyl 6-[bis[2-(tert-butoxycarbonylamino)ethyl]amino]-6-oxohexanoate

Conditions	Yield
Stage #1: adipic acid monomethyl ester With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Stage #2: bis(2-tert-butyloxycarbonylaminoethyl)amine In dichloromethane at 20℃;	96%

adipic acid monomethyl ester (627-91-8) + 1-dodecylthiol (112-55-0) → C17H32O3S

Conditions	Yield
Stage #1: adipic acid monomethyl ester With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 10℃; for 0.166667h; Stage #2: 1-dodecylthiol In acetonitrile at 25℃; for 22h;	96%

adipic acid monomethyl ester (627-91-8) + aniline (62-53-3) → 6-oxo-6-(phenylamino)-hexanoic acid methyl ester (64785-82-6)

Conditions	Yield
Stage #1: adipic acid monomethyl ester With 1-methyl-1H-imidazole; p-toluenesulfonyl chloride In acetonitrile at 0 - 5℃; for 0.5h; Stage #2: aniline In acetonitrile at 0 - 5℃; for 2h; Further stages.;	95%
With 1-(tert-butoxy)-2-(tert-butoxy)carbonyl-1,2-dihydroisoquinoline In dichloromethane at 20℃; for 24h;	92%
With triethylamine In dichloromethane for 12h; Heating;	81%
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-hydroxybenzotriazol-hydrate In dichloromethane at 20℃; for 4h;	58%

adipic acid monomethyl ester (627-91-8) + [(glycyl)glycyl]glycine tert-butyl ester (165282-99-5) → C17H29N3O7

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃;	95%

bis(η5-cyclopentadienyl)ruthenium (1287-13-4) + adipic acid monomethyl ester (627-91-8) → methyl 5-ruthenocenoylpentanoate

Conditions	Yield
With trifluorormethanesulfonic acid; trifluoroacetic anhydride In dichloromethane at 20℃; for 2h; Inert atmosphere; Schlenk technique;	95%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + adipic acid monomethyl ester (627-91-8) → 1-methyl 6-succinimidyl adipate (118380-06-6)

Conditions	Yield
With dicyclohexyl-carbodiimide In acetone at 20℃; for 2h;	94%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; Esterification;
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine
With triethylamine In thionyl chloride; dichloromethane

piperidine (110-89-4) + adipic acid monomethyl ester (627-91-8) → 6-oxo-6-(piperidino)-hexanoic acid methyl ester

Conditions	Yield
Stage #1: adipic acid monomethyl ester With 1-methyl-1H-imidazole; p-toluenesulfonyl chloride In acetonitrile at 0 - 5℃; for 0.5h; Stage #2: piperidine In acetonitrile at 0 - 5℃; for 2h; Further stages.;	94%
With 1-(tert-butoxy)-2-(tert-butoxy)carbonyl-1,2-dihydroisoquinoline In dichloromethane at 20℃; for 24h;	88%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	82%

adipic acid monomethyl ester (627-91-8) + 1,2,3-trimethoxybenzene (634-36-6) → 6-Oxo-6-(2,3,4-trimethoxy-phenyl)-hexanoic acid methyl ester (917591-96-9)

Conditions	Yield
With PPA; Polyphosphoric acid (PPA) at 45℃; for 2.5h;	93%

N-p-toluenesulfonylpyrrole (17639-64-4) + adipic acid monomethyl ester (627-91-8) → C18H21NO5S (1093430-77-3)

Conditions	Yield
With trifluoroacetic anhydride In dichloromethane for 48h; Reflux; Inert atmosphere;	93%

adipic acid monomethyl ester (627-91-8) + Ala-Thr-Leu-Asn-Phe-OMe trifluoroacetate → 5-[1-(1-{1-[2-carboxy-1-(1-methoxycarbonyl-2-phenylethylcarbamoyl)ethylcarbamoyl]-3-methylbutylcarbamoyl}-2-hydroxypropylcarbamoyl)ethylcarbamoyl] methyl pentanoate

Conditions	Yield
With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol In N,N-dimethyl-formamide at 20℃; for 12h;	92%

oxalyl dichloride (79-37-8) + adipic acid monomethyl ester (627-91-8) → 5-Methoxycarbonylpentansaeure-tert-butylester (52221-08-6)

Conditions	Yield
With pyridine In N-methyl-acetamide; dichloromethane; tert-butyl alcohol	92%
With pyridine In N-methyl-acetamide; dichloromethane; tert-butyl alcohol	92%

adipic acid monomethyl ester (627-91-8) + 3-α-acetoxy-4-β-amino-24-norurs-12-ene (108015-89-0) → methyl 6-((3-α-acetoxy-24-norurs-12-en-4-yl)amino)-6-oxohexanoate

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran at 0 - 20℃; for 16.5h;	92%

furan (110-00-9) + adipic acid monomethyl ester (627-91-8) → 5-(2-Furoyl)pentansaeure-methylester (91971-41-4)

Conditions	Yield
With boron trifluoride diethyl etherate; trifluoroacetic anhydride In toluene at 0 - 10℃; for 4h; Reagent/catalyst;	92%
With boron trifluoride diethyl etherate; trifluoroacetic anhydride In toluene at 0 - 10℃; for 4h; Reagent/catalyst;	92%

adipic acid monomethyl ester (627-91-8) + N-(tert-butoxycarbonyl)-1,4-phenylenediamine (71026-66-9) → methyl 6-((4-((tert-butoxycarbonyl)amino)phenyl)amino)-6-oxohexanoate

Conditions	Yield
Stage #1: adipic acid monomethyl ester With 4-methyl-morpholine; chloroformic acid ethyl ester In dichloromethane at 0℃; for 0.25h; Stage #2: N-(tert-butoxycarbonyl)-1,4-phenylenediamine In dichloromethane at 20℃;	92%

adipic acid monomethyl ester (627-91-8) + N,N''-di-Z-diethylenetriamine (160256-75-7) → C27H35N3O7

Conditions	Yield
Stage #1: adipic acid monomethyl ester With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Stage #2: N,N''-di-Z-diethylenetriamine In dichloromethane at 20℃; for 20h;	91.6%

Upstream product

• 124-04-9 Adipic acid 
• 627-93-0 hexanedioic acid dimethyl ester 
• 2525-16-8 O-methylcaprolactim 
• 67-56-1 methanol 
• 10316-66-2 2-hydroxy-2-cyclohexen-1-one 
• 77-78-1 dimethyl sulfate 
• 4883-67-4 2-nitrocyclohexanone 
• 2979-24-0 2-methoxycyclohexanol 
• 13865-19-5 4-oxobutanoic acid methyl ester 
• 89898-52-2 (E)-Hex-2-enedioic acid 6-methyl ester 
• 108-94-1 cyclohexanone 
• 108-93-0 cyclohexanol 
• 2035-75-8 adipic anhydride 
• 1119-72-8 cis,cis-Muconic acid 

Downstream Products

• 17351-34-7 pentadec-14-enoic acid 
• 2969-87-1 Vinyl-methyl-adipat 
• 63880-87-5 methyl 3'-carboxy-2',4',6'-triiodo-5'-(N-methylacetamido)adipanilate 
• 14296-16-3 1,20-dibromoeicosane 
• 41240-56-6 15-bromopentadecanoic acid methyl ester 
• 106-79-6 dimethyl sebacate 
• 34540-49-3 1,22-dibromodocosane 
• 26825-89-8 methyl 16-bromohexadecanoate 
• 4617-33-8 15-hydroxylpentadecanoic acid 
• 506-13-8 16-hydroxyhexadecanoic acid 
• 1191-25-9 6-Hydroxyhexanoic acid 
• 35444-44-1 methyl adipoyl chloride 
• 6946-69-6 Methyl N,N-dipropyladipamat 
• 627-93-0 hexanedioic acid dimethyl ester 

Relevant articles and documents

Oxidation of cyclohexanone and/or cyclohexanol catalyzed by Dawson-type polyoxometalates using hydrogen peroxide

The oxidation of cyclohexanone, cyclohexanol or cyclohexanone/cyclohexanol mixture using as catalyst, Dawson-type polyoxometalates (POMs) of formula, α- and β-K6P2W18O62, α-K6P2Mo6W12O62 and α1-K7P2Mo5VW12O62 and hydrogen peroxide, carried out at 90 °C with a reaction time of 20 h, led to a high number of mono- and di-acids which were identified by GC-MS. Levulinic, 6-hydroxyhexanoic, adipic, glutaric and succinic acids, major products were evaluated by HPLC. Regardless of the substrate nature, all POMs exhibited high catalytic activity with 94–99% of conversion, whereas the formation of the different products is sensitively related to both the composition and symmetry of the POMs and the substrate nature. The main products are adipic acid in the presence of α-K6P2Mo6W12O62 and α1-K7P2Mo5VW12O62, levulinic acid in the presence of α1-K7P2Mo5VW12O62 and β-K6P2W18O62 and 6-hydroxyhexanoic acid in the presence of α- and β-K6P2W18O62. Graphical abstract: High catalytic activity was observed with?α- and?β-K6P2W18O62, α-K6P2Mo6W12O62 and α1-K7P2Mo5VW12O62 Dawson-type for the oxidation of cyclohexanone, cyclohexanol or cyclohexanone/cyclohexanol mixture, in the hydrogen peroxide presence, to several oxygenated products. Adipic, levulinic and 6-hydroxyhexanoic acids are the main products. The peroxo- species formed in situ could be the active sites.[Figure not available: see fulltext.]

Discovery of 6-Oxo-4-phenyl-hexanoic acid derivatives as RORγt inverse agonists showing favorable ADME profile

The retinoic acid receptor-related orphan nuclear receptor gamma t (RORγt), which is a promising therapeutic target for immune diseases, is a major transcription factor of genes related to psoriasis pathogenesis, such as interleukin (IL)-17A, IL-22, and IL-23R. Inspired by the co-crystal structure of RORγt, a 6-oxo-4-phenyl-hexanoic acid derivative 6a was designed, synthesized, and identified as a ligand of RORγt. The structure–activity relationship (SAR) studies in 6a, which focus on the improvement of its membrane permeability profile by introducing chlorine atoms, led to finding 12a, which has a potent RORγt inhibitory activity and a favorable pharmacokinetic profile.

NOVEL ESTERIFICATION CATALYST AND USES THEREOF

Tin (II) glucarate is found to be effective alone and in combination with other tin compounds for catalyzing the reaction of carboxylic acids such as furan-2,5-dicarboxylic acid, terephthalic acid and adipic acid with alcohols such as the C1-C3 alcohols.