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[ CAS No. 4100-80-5 ] {[proInfo.proName]}

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Chemical Structure| 4100-80-5
Chemical Structure| 4100-80-5
Structure of 4100-80-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4100-80-5 ]

CAS No. :4100-80-5 MDL No. :MFCD00005527
Formula : C5H6O3 Boiling Point : -
Linear Structure Formula :- InChI Key :DFATXMYLKPCSCX-UHFFFAOYSA-N
M.W : 114.10 Pubchem ID :20051
Synonyms :

Calculated chemistry of [ 4100-80-5 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.6
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 25.52
TPSA : 43.37 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.91
Log Po/w (XLOGP3) : 0.11
Log Po/w (WLOGP) : 0.1
Log Po/w (MLOGP) : 0.33
Log Po/w (SILICOS-IT) : 0.99
Consensus Log Po/w : 0.49

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.62
Solubility : 27.6 mg/ml ; 0.242 mol/l
Class : Very soluble
Log S (Ali) : -0.58
Solubility : 30.3 mg/ml ; 0.265 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.61
Solubility : 28.2 mg/ml ; 0.247 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.73

Safety of [ 4100-80-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4100-80-5 ]

* 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.

  • Downstream synthetic route of [ 4100-80-5 ]

[ 4100-80-5 ] Synthesis Path-Downstream   1~84

  • 1
  • [ 636-60-2 ]
  • [ 4100-80-5 ]
YieldReaction ConditionsOperation in experiment
96% With oxalyl dichloride; N,N-dimethyl-formamide In toluene for 3h; Inert atmosphere; Reflux; General procedure for the preparation of cyclic anhydrides 1a-v General procedure: Dicarboxylic acid 2 (1 mmol) and oxalyl chloride (1.2 mmol) were combined in dry toluene (5 mL) and a drop of freshly distilled DMF was added. The reaction vessel was purged with argon and the reaction was heated under stirring for 3 h. The stirring was stopped and the toluene solution was decanted off the oily residue and filtered. Evaporation of the volatiles provided the analytically pure target product which, if necessary, was transformed intro crystalline form by trituration with diethyl ether. In some cases (see ESI) additional crystallization or trituration with 1:2 v/v hexane-toluene mixture was used. .
88.2% With acetic anhydride for 4h; Reflux; The mixture of 2-methylsuccinic acid (2.0g, 15mmol) and acetic anhydride (10.8g, 90mmol) wasrefluxed for 4 hours and then was evaporated under reduced pressure. The resulting residue waspurified by recrystallization in toluene (3mL) in the freezer to yield 2-methyl succinic anhydrideas a white solid (1.5g, 88.2%)
With acetyl chloride
at 200℃; inactive form;
With diphosphorus pentasulfide inactive form;
With acetyl chloride inactive form;
With acetic anhydride
With oxalyl dichloride for 0.333333h; Heating;
With 4-methyl-morpholine; methyl chloroformate In tetrahydrofuran at 20℃; for 0.25h;
at 66.9℃; -ΔΔH;
With acetyl chloride

  • 2
  • [ 4100-80-5 ]
  • [ 71-43-2 ]
  • [ 7315-67-5 ]
  • [ 1771-65-9 ]
YieldReaction ConditionsOperation in experiment
1: 62% 2: 39% With aluminium trichloride at 40℃; for 2h;
With aluminium trichloride
  • 3
  • [ 4100-80-5 ]
  • [ 71-43-2 ]
  • [ 1771-65-9 ]
YieldReaction ConditionsOperation in experiment
75%
68% With aluminium trichloride In benzene 1) 20 deg C, 3 h, 2) 45 deg C, 1 h;
With aluminium trichloride Zers. des Reaktionsprodukts durch verd. Salzsaeure;
With aluminium trichloride
With aluminium trichloride In dichloromethane
With aluminium trichloride; nitromethane
With aluminium trichloride
With aluminium trichloride

  • 4
  • [ 6738-23-4 ]
  • [ 4100-80-5 ]
  • 4-(5-methoxy-2,4-dimethyl-phenyl)-2-methyl-4-oxo-butyric acid [ No CAS ]
  • 6
  • [ 1706-11-2 ]
  • [ 4100-80-5 ]
  • [ 154406-43-6 ]
  • 7
  • [ 1706-11-2 ]
  • [ 4100-80-5 ]
  • [ 855153-33-2 ]
  • 8
  • [ 92-52-4 ]
  • [ 4100-80-5 ]
  • [ 67959-67-5 ]
YieldReaction ConditionsOperation in experiment
83% With aluminium trichloride In 1,2-dichloro-ethane 1) 20 deg C, 3 h, 2) 45 deg C, 1 h;
60% With aluminium trichloride In nitrobenzene for 4h; Ambient temperature;
With aluminium trichloride In nitrobenzene at 5℃;
With aluminium trichloride

  • 9
  • [ 75-77-4 ]
  • [ 4100-80-5 ]
  • [ 77220-07-6 ]
YieldReaction ConditionsOperation in experiment
97% With triethylamine; zinc(II) chloride In acetonitrile Ambient temperature;
95% With triethylamine; zinc(II) chloride In acetonitrile
  • 10
  • [ 27607-77-8 ]
  • [ 4100-80-5 ]
  • [ 77220-07-6 ]
YieldReaction ConditionsOperation in experiment
56% With triethylamine In diethyl ether for 0.5h; Ambient temperature;
  • 11
  • [ 827-52-1 ]
  • [ 4100-80-5 ]
  • [ 91121-68-5 ]
  • 12
  • [ 206-44-0 ]
  • [ 4100-80-5 ]
  • [ 95741-73-4 ]
YieldReaction ConditionsOperation in experiment
60% With aluminium trichloride In nitrobenzene for 6h; Ambient temperature;
  • 13
  • [ 37847-52-2 ]
  • [ 4100-80-5 ]
  • 4-(2',4'-difluorobiphenyl-4-yl)-3-methyl-4-oxobutanoic acid [ No CAS ]
  • [ 112344-52-2 ]
  • 14
  • [ 140714-28-9 ]
  • [ 4100-80-5 ]
  • [ 140234-93-1 ]
YieldReaction ConditionsOperation in experiment
95% With triethylamine In dichloromethane at 20℃; for 0.25h;
  • 15
  • [ 103-84-4 ]
  • [ 4100-80-5 ]
  • [ 52240-23-0 ]
YieldReaction ConditionsOperation in experiment
42% Stage #1: Acetanilid; 2-methylsuccinic anhydride With aluminum (III) chloride In N,N-dimethyl-formamide at 60 - 80℃; for 3h; Stage #2: With hydrogenchloride; water In N,N-dimethyl-formamide at 20℃; A28 4-(4-acetylaminophenyl)-2-methyl-4-oxobutanoic acid EXAMPLE A284-(4-acetylaminophenyl)-2-methyl-4-oxobutanoic acid22 ml (0.28 mol) of dimethylformamide were added dropwise to 133.34 g (1.0 mol) of finely powdered aluminium chloride within 20 minutes, while cooling externally with ice. After the strongly exothermic reaction died down, 13.517 g (0.1 mol) of acetanilide and 11.413 g (0.1 mol) of methylsuccinic acid anhydride were added all at once and at an initial temperature of 60° C., during which time the mixture heated up to about 80° C. It was kept for another 3 hours at a temperature of 60-70° C., the still hot mixture was stirred into 1 kg of crushed ice, 60 ml, of conc. hydrochloric acid were added and the mixture was left to stand overnight at ambient temperature. The precipitate formed was suction filtered and thoroughly washed with water. It was taken up in 150 ml of methanol, stirred for 30 minutes at 50° C., then for another 30 minutes while cooling externally with ice and the precipitate was suction filtered. After drying in a circulating air dryer at 60° C., 10.4 g (42% of theoretical) of colourless crystals were obtained, m.p. 229-231° C. and Rf 0.48 (El I).IR (KBr): 1714.6, 1662.5 cm-1 (CO)
40% With aluminium trichloride In N,N-dimethyl-formamide at 70℃; for 1.5h;
  • 16
  • [ 1706-11-2 ]
  • [ 4100-80-5 ]
  • [ 4773-88-0 ]
  • [ 154406-43-6 ]
  • 17
  • [ 67836-91-3 ]
  • [ 4100-80-5 ]
  • 2-(3-Methyl-2,5-dioxo-pyrrolidin-1-yl)-benzoic acid 2,2-dimethyl-propyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,1'-carbonyldiimidazole In dichloromethane at 25℃; for 23h;
  • 18
  • [ 41827-15-0 ]
  • [ 4100-80-5 ]
  • [ 63213-32-1 ]
YieldReaction ConditionsOperation in experiment
With aluminium trichloride In tetrachloromethane
  • 19
  • 4-(2,3-dihydro-1,4-benzodioxin-5-yl)-1-piperazineethanamine trihydrochloride [ No CAS ]
  • [ 4100-80-5 ]
  • 1-<2-<4-(2,3-dihydro-1,4-benzodioxin-5-yl)-1-piperazinyl>ethyl>-3-methyl-2,5-pyrrolidinedione [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With N-ethyl-N,N-diisopropylamine In toluene for 16h; Heating;
  • 20
  • [ 4100-80-5 ]
  • [ 2938-98-9 ]
YieldReaction ConditionsOperation in experiment
54.6% With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Heating;
28.5 g With lithium aluminium tetrahydride In tetrahydrofuran for 48h; 5 To a glass flask, 101.2 g (766 mmol) of methyl succinic acid was added, and 400 mL of acetyl chloride was added dropwise. After stirring for 2 hours,Purify by vacuum distillation after concentration,83.6 g of methyl succinic anhydride was obtained.To a glass flask, 26.3 g (705 mmol) of lithium aluminum hydride and 800 mL of tetrahydrofuran were added, and this was dissolved in 200 mL of tetrahydrofuran.41.0 g (359 mmol) of succinic anhydride was added dropwise over 1 hour. After stirring for 2 days, a mixture of 100 mL of tetrahydrofuran and 100 mL of water was added dropwise, and 500 mL of tetrahydrofuran was added to the resulting slurry. After drying with sodium sulfate, the solvent was distilled off. The obtained crude product was distilled to obtain 28.5 g of 2-methyl-1,4-butanediol. *
  • 21
  • 2-Amino-benzoic acid (1R,5S)-3-ethyl-9-hydroxy-9-[(Z)-2-((1R,3S)-1-hydroxy-3-methoxy-cyclohexyl)-vinyl]-3-aza-bicyclo[3.3.1]non-1-ylmethyl ester [ No CAS ]
  • [ 4100-80-5 ]
  • 2-(3-Methyl-2,5-dioxo-pyrrolidin-1-yl)-benzoic acid (1S,5R)-3-ethyl-9-hydroxy-9-[(Z)-2-((1S,3R)-1-hydroxy-3-methoxy-cyclohexyl)-vinyl]-3-aza-bicyclo[3.3.1]non-1-ylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 48h; Yield given;
  • 22
  • 2-Amino-benzoic acid (1R,5S)-3-ethyl-9-hydroxy-9-[(E)-2-((1R,3S)-1-hydroxy-3-methoxy-cyclohexyl)-vinyl]-3-aza-bicyclo[3.3.1]non-1-ylmethyl ester [ No CAS ]
  • [ 4100-80-5 ]
  • 2-(3-Methyl-2,5-dioxo-pyrrolidin-1-yl)-benzoic acid (1S,5R)-3-ethyl-9-hydroxy-9-[(E)-2-((1S,3R)-1-hydroxy-3-methoxy-cyclohexyl)-vinyl]-3-aza-bicyclo[3.3.1]non-1-ylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 48h; Yield given;
  • 23
  • 2-Amino-benzoic acid (1R,5S)-3-ethyl-9-hydroxy-9-[(Z)-2-((1S,3S)-1-hydroxy-3-methoxy-cyclohexyl)-vinyl]-3-aza-bicyclo[3.3.1]non-1-ylmethyl ester [ No CAS ]
  • [ 4100-80-5 ]
  • 2-(3-Methyl-2,5-dioxo-pyrrolidin-1-yl)-benzoic acid (1S,5R)-3-ethyl-9-hydroxy-9-[(Z)-2-((1R,3R)-1-hydroxy-3-methoxy-cyclohexyl)-vinyl]-3-aza-bicyclo[3.3.1]non-1-ylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 48h; Yield given;
  • 24
  • 2-Amino-benzoic acid (1R,5S)-3-ethyl-9-hydroxy-9-[(E)-2-((1S,3S)-1-hydroxy-3-methoxy-cyclohexyl)-vinyl]-3-aza-bicyclo[3.3.1]non-1-ylmethyl ester [ No CAS ]
  • [ 4100-80-5 ]
  • 2-(3-Methyl-2,5-dioxo-pyrrolidin-1-yl)-benzoic acid (1S,5R)-3-ethyl-9-hydroxy-9-[(E)-2-((1R,3R)-1-hydroxy-3-methoxy-cyclohexyl)-vinyl]-3-aza-bicyclo[3.3.1]non-1-ylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 48h; Yield given;
  • 25
  • 2-Amino-benzoic acid (1R,5S)-3-ethyl-9-hydroxy-9-((1R,3S)-1-hydroxy-3-methoxy-cyclohexylethynyl)-3-aza-bicyclo[3.3.1]non-1-ylmethyl ester [ No CAS ]
  • [ 4100-80-5 ]
  • 2-(3-Methyl-2,5-dioxo-pyrrolidin-1-yl)-benzoic acid (1S,5R)-3-ethyl-9-hydroxy-9-((1S,3R)-1-hydroxy-3-methoxy-cyclohexylethynyl)-3-aza-bicyclo[3.3.1]non-1-ylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 48h; Yield given;
  • 26
  • 2-Amino-benzoic acid (1R,5S)-3-ethyl-9-hydroxy-9-((1S,3S)-1-hydroxy-3-methoxy-cyclohexylethynyl)-3-aza-bicyclo[3.3.1]non-1-ylmethyl ester [ No CAS ]
  • [ 4100-80-5 ]
  • 2-(3-Methyl-2,5-dioxo-pyrrolidin-1-yl)-benzoic acid (1S,5R)-3-ethyl-9-hydroxy-9-((1R,3R)-1-hydroxy-3-methoxy-cyclohexylethynyl)-3-aza-bicyclo[3.3.1]non-1-ylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 48h; Yield given;
  • 27
  • [ 2687-43-6 ]
  • [ 4100-80-5 ]
  • [ 214679-32-0 ]
YieldReaction ConditionsOperation in experiment
69% Stage #1: O-benzylhydoxylamine hydrochloride; 2-methylsuccinic anhydride With 4-methyl-morpholine In toluene at 20℃; for 2.5h; Reflux; Stage #2: With acetic acid for 6h; Reflux; 41.1 Step 1: Preparation of l-(benzyloxy)-3-methylpyrrolidine-2,5-dione Step 1: Preparation of l-(benzyloxy)-3-methylpyrrolidine-2,5-dione [00173] To a stirring solution of 3-methyldihydrofuran-2,5-dione (1.09 g, 9.55 mmol, 1.0 equiv) and N-methylmorpholine (1.93 g, 19.1 mmol, 2.0 equiv) in anhydrous toluene (50 mL) was added O-benzylhydroxylamine hydrochloride (1.52 g, 9.55 mmol, 1.0 equiv). The mixture was stirred for 30 min at room temperature and then heated to reflux with azeotropic removal of water. After 2 h, glacial acetic acid (1.0 mL) was added to the reaction mixture. After refluxing for 6 h, the reaction was cooled to room temperature, and the product was extracted from saturated aHC03 (200 mL) with EtOAc (3 x 200 mL). The combined organic layers were dried over anhydrous Na2S04 and concentrated under vacuum. The crude product was purified by S1O2 chromatography (40% EtOAc/Hexanes) to yield the title compound as a white solid (1.44 g, 6.56 mmol, 69%): XH NMR (500 MHz, Chloroform-if) δ 7.46 (t, J= 4.81 Hz, 2H), 7.41 - 7.32 (m, 3H), 5.11 (s, 2H), 2.82 (dd, J= 8.96, 17.69 Hz, 1H), 2.78 - 2.69 (m, 1H), 2.19 (dd, J= 3.93, 17.74 Hz, 1H), 1.24 (d, J= 7.29 Hz, 3H); ljC NMR (126 MHz, Chloroform- if) δ 175.05, 170.97, 133.64, 130.44, 129.84, 128.89, 78.84, 34.15, 32.35, 17.10.
With 4-methyl-morpholine; 1,1'-carbonyldiimidazole 1.) CH2Cl2, r.t., overnight, 2.) CH2Cl2, r.t., 2 h; reflux, 30 min; Yield given. Multistep reaction;
  • 28
  • [ 104-72-3 ]
  • [ 4100-80-5 ]
  • 4-(4-Decyl-phenyl)-2-methyl-4-oxo-butyric acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With aluminium trichloride In dichloromethane; nitrobenzene for 1h; Ambient temperature;
  • 29
  • [ 123-01-3 ]
  • [ 4100-80-5 ]
  • 4-(4-Dodecyl-phenyl)-2-methyl-4-oxo-butyric acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With aluminium trichloride In dichloromethane; nitrobenzene for 1h; Ambient temperature;
  • 30
  • [ 1459-09-2 ]
  • [ 4100-80-5 ]
  • 4-(4-Hexadecyl-phenyl)-2-methyl-4-oxo-butyric acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With aluminium trichloride In dichloromethane; nitrobenzene for 1h; Ambient temperature;
  • 31
  • [ 82185-41-9 ]
  • [ 4100-80-5 ]
  • benzyl 2-(3-methyl-2,5-dioxopyrrolidin-1-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% at 125℃; for 3h;
54% With 1,1'-carbonyldiimidazole In dichloromethane Ambient temperature;
  • 33
  • [ 554-14-3 ]
  • [ 4100-80-5 ]
  • [ 248254-74-2 ]
YieldReaction ConditionsOperation in experiment
74% With aluminium trichloride In dichloromethane at 0 - 20℃; for 1h;
  • 34
  • [ 7779-16-0 ]
  • [ 4100-80-5 ]
  • cyclohexyl 2-(3-methyl-2,5-dioxopyrrolidin-1-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With dmap In N,N-dimethyl-formamide at 125℃;
70% at 125℃; for 3h;
  • 35
  • [ 4100-80-5 ]
  • 2-Amino-benzoic acid (1S,5S)-3-ethyl-9-methylene-3-aza-bicyclo[3.3.1]non-1-ylmethyl ester [ No CAS ]
  • 2-(3-Methyl-2,5-dioxo-pyrrolidin-1-yl)-benzoic acid (1S,5S)-3-ethyl-9-methylene-3-aza-bicyclo[3.3.1]non-1-ylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With dmap In N,N-dimethyl-formamide at 125℃;
  • 36
  • [ 67-56-1 ]
  • [ 4100-80-5 ]
  • [ 83509-04-0 ]
  • [ 111266-16-1 ]
YieldReaction ConditionsOperation in experiment
With modified cinchona alkaloid (DHQD)2AQN In diethyl ether at 25℃; for 4h; Title compound not separated from byproducts.;
  • 37
  • [ 67-56-1 ]
  • [ 4100-80-5 ]
  • [ 23268-03-3 ]
  • [ 111266-27-4 ]
  • 38
  • [ 71-23-8 ]
  • [ 4100-80-5 ]
  • (R)-2-Methyl-succinic acid 1-propyl ester [ No CAS ]
  • (S)-2-Methyl-succinic acid 1-propyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With modified cinchona alkaloid (DHQD)2AQN In diethyl ether at 25℃; for 4h; Title compound not separated from byproducts.;
  • 39
  • [ 71-23-8 ]
  • [ 4100-80-5 ]
  • (S)-2-Methyl-succinic acid 4-propyl ester [ No CAS ]
  • (R)-2-methyl-succinic acid 4-propyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With modified cinchona alkaloid (DHQD)2AQN In diethyl ether at 25℃; for 4h; Title compound not separated from byproducts.;
  • 40
  • [ 64-17-5 ]
  • [ 4100-80-5 ]
  • [ 133695-54-2 ]
  • (R)-1-Ethyl 4-hydrogen 2-methylbutanedioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With modified cinchona alkaloid (DHQD)2AQN In diethyl ether at 25℃; for 4h; Title compound not separated from byproducts.;
  • 41
  • [ 64-17-5 ]
  • [ 4100-80-5 ]
  • (R)-2-methyl-succinic acid 4-ethyl ester [ No CAS ]
  • (S)-2-Methyl-succinic acid 4-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With modified cinchona alkaloid (DHQD)2AQN In diethyl ether at 25℃; for 4h; Title compound not separated from byproducts.;
  • 42
  • [ 2859-78-1 ]
  • [ 4100-80-5 ]
  • [ 358369-06-9 ]
  • 2-methyl-4-oxo-4-(3,4-dimethoxyphenyl)-butyric acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-Bromoveratrole With magnesium In tetrahydrofuran at 60℃; for 5h; Stage #2: 2-methylsuccinic anhydride In tetrahydrofuran at 0 - 20℃; Further stages. Title compound not separated from byproducts.;
  • 43
  • [ 2859-78-1 ]
  • [ 100-63-0 ]
  • [ 4100-80-5 ]
  • 6-(3,4-dimethoxy-phenyl)-4-methyl-2-phenyl-4,5-dihydro-2<i>H</i>-pyridazin-3-one [ No CAS ]
  • 6-(3,4-dimethoxy-phenyl)-5-methyl-2-phenyl-4,5-dihydro-2<i>H</i>-pyridazin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 0.44 g 2: 70 mg Stage #1: 4-Bromoveratrole With magnesium In tetrahydrofuran at 60℃; for 5h; Stage #2: phenylhydrazine; 2-methylsuccinic anhydride In tetrahydrofuran at 0 - 20℃; Stage #3: phenylhydrazine In toluene Heating; Further stages.;
  • 44
  • [ 4100-80-5 ]
  • (+/-)-(1'S,7'R,8'S)-(10-ethyl-7-hydroxy-10-azatricyclo[6.3.3.01,7]tetradec-4-ene-8-yl)methyl 2-aminobenzoate [ No CAS ]
  • (+/-)-(1''S,7''R,8''S,3'RS)-(10-ethyl-7-hydroxy-10-azatricyclo[6.3.3.01,7]tetradec-4-ene-8-yl)methyl 2-(3-methyl-2,5-dioxopyrrolidin-1-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% at 125℃;
  • 45
  • 4-methyloxetan-2-one [ No CAS ]
  • [ 201230-82-2 ]
  • [ 4100-80-5 ]
YieldReaction ConditionsOperation in experiment
95% With ({1,2-di[(2-OH-3,5-di-tBu)PhCH=N]Ph}Al[THF]2)+[Co(CO)4]- In toluene at 55℃; for 24h;
In 1,4-dioxane at 40℃;
With Co(CO)4⊂Cr-MIL-101 MOF; silicon carbide powder In toluene at 40℃; for 60h; Inert atmosphere; Glovebox; Flow reactor; chemoselective reaction;
  • 46
  • [ 4100-80-5 ]
  • [ 337308-69-7 ]
  • 3-(dimethylamino)propyl 2-(3-methyl-2,5-dioxopyrrolini-1-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% at 125℃; for 3h;
  • 47
  • [ 4100-80-5 ]
  • [ 337308-68-6 ]
  • 1-methyl-piperidin-3-ylmethyl 2-(3-methyl-2,5-dioxopyrrolidin-1-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% at 125℃; for 3h;
  • 48
  • [ 4100-80-5 ]
  • C32H37N3O4 [ No CAS ]
  • C42H45N3O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% at 125℃;
  • 49
  • (1RS,5SR,9SR)-9-[(2-aminobenzoyl)oxy]-3-(3-phenylpropyl)-3-azabicyclo[3.3.1]non-1-ylmethyl 2-aminobenzoate [ No CAS ]
  • [ 4100-80-5 ]
  • (1RS,5SR,9SR)-9-(2-[3-methyl-2,5-dioxopyrrolidin-1-yl]benzoyl)-3-(3-phenylpropyl)-3-azabicyclo[3.3.1]non-1-ylmethyl 2-(3-methyl-2,5-dioxopyrrolidin-1-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% at 125℃; for 4h;
  • 50
  • (1SR,7SR,8SR)-{10-(3-phenylpropyl)-6-oxa-10-azatricyclo[6.3.3.01,7]tetradec-3-en-8-yl}methyl 2-aminobenzoate [ No CAS ]
  • [ 4100-80-5 ]
  • (1SR,7SR,8SR)-{10-(3-phenylpropyl)-6-oxa-10-azatricyclo[6.3.3.01,7]tetradec-3-en-8-yl}methyl 2-(3-methyl-2,5-dioxopyrrolidin-1-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% at 125℃; for 4h;
  • 51
  • [ 75-89-8 ]
  • [ 4100-80-5 ]
  • (R)-2-Methyl-succinic acid 1-(2,2,2-trifluoro-ethyl) ester [ No CAS ]
  • (S)-2-Methyl-succinic acid 1-(2,2,2-trifluoro-ethyl) ester [ No CAS ]
  • (S)-2-Methyl-succinic acid 4-(2,2,2-trifluoro-ethyl) ester [ No CAS ]
  • (R)-2-Methyl-succinic acid 4-(2,2,2-trifluoro-ethyl) ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With modified cinchona alkaloid (DHQD)2AQN In diethyl ether at -24℃;
  • 52
  • [ 201230-82-2 ]
  • [ 100-28-7 ]
  • [ 16033-71-9 ]
  • 4-methyloxetan-2-one [ No CAS ]
  • 6-methyl-3-(4-nitrophenyl)-1,3-oxazinane-2,4-dione [ No CAS ]
  • [ 4100-80-5 ]
YieldReaction ConditionsOperation in experiment
1: 7 % Spectr. 2: 48 % Spectr. 3: 45 % Spectr. In 1,4-dioxane at 40℃; for 24h; Title compound not separated from byproducts.;
  • 53
  • [ 201230-82-2 ]
  • [ 16033-71-9 ]
  • [ 4100-80-5 ]
YieldReaction ConditionsOperation in experiment
99 % Spectr. In 1,4-dioxane at 90℃; for 3h;
With dicobalt octacarbonyl; C72H96Cl3Cr3N6O6 at 80℃; for 18h; Autoclave; regioselective reaction;
  • 54
  • [ 4100-80-5 ]
  • 6-(3,4-dimethoxy-phenyl)-5-methyl-4,5-dihydro-2<i>H</i>-pyridazin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: Mg / tetrahydrofuran / 5 h / 60 °C 1.2: tetrahydrofuran / 0 - 20 °C 2.1: 80 percent / NH2NH2*H2O / ethanol / 4 h / Heating
  • 55
  • [ 4100-80-5 ]
  • 6-(3,4-dimethoxy-phenyl)-5-methyl-2-phenyl-4,5-dihydro-2<i>H</i>-pyridazin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: Mg / tetrahydrofuran / 5 h / 60 °C 1.2: tetrahydrofuran / 0 - 20 °C 2.1: 57 percent / toluene / Heating
  • 56
  • [ 4100-80-5 ]
  • [ 52239-91-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aluminum chloride 2: hydrazine / ethanol / Heating
Multi-step reaction with 2 steps 1: AlCl3 / Zers. des Reaktionsprodukts durch verd. Salzsaeure 2: diluted NaOH-solution; hydrazine sulfate
  • 57
  • [ 4100-80-5 ]
  • [ 103853-58-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: aluminum chloride 2: hydrazine / ethanol / Heating 3: LiAlH4 / tetrahydrofuran
  • 58
  • [ 4100-80-5 ]
  • (R,S)-1-(3,4-dichlorobenzoyl)-5-methyl-3-phenyl-1,4,5,6-tetrahydropyridazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: aluminum chloride 2: hydrazine / ethanol / Heating 3: LiAlH4 / tetrahydrofuran 4: toluene / 1.5 h / Heating
  • 59
  • [ 4100-80-5 ]
  • [ 53885-72-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 40 percent / AlCl3 / dimethylformamide / 1.5 h / 70 °C 2: 93 percent / conc. HCl / 0.25 h / Heating
  • 60
  • [ 4100-80-5 ]
  • [ 53885-82-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 40 percent / AlCl3 / dimethylformamide / 1.5 h / 70 °C 2: 93 percent / conc. HCl / 0.25 h / Heating 3: 66 percent / hydrazine hydrate / H2O / 3 h / 100 °C 4: 92 percent / toluene / 6 h / Heating
  • 61
  • [ 4100-80-5 ]
  • [ 85221-83-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 40 percent / AlCl3 / dimethylformamide / 1.5 h / 70 °C 2: 93 percent / conc. HCl / 0.25 h / Heating 3: 66 percent / hydrazine hydrate / H2O / 3 h / 100 °C 4: 52 percent / tetrahydrofuran / 6 h / Heating
  • 62
  • [ 4100-80-5 ]
  • [ 52239-87-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 40 percent / AlCl3 / dimethylformamide / 1.5 h / 70 °C 2: 93 percent / conc. HCl / 0.25 h / Heating 3: 66 percent / hydrazine hydrate / H2O / 3 h / 100 °C
  • 63
  • [ 4100-80-5 ]
  • [ 59324-71-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 60 percent / anhydr. aluminum chloride / nitrobenzene / 4 h / Ambient temperature 2: 75 percent / zinc amalgam, conc. HCl / H2O; toluene / 0.17 h / Heating
Multi-step reaction with 3 steps 1: 60 percent / anhydr. aluminum chloride / nitrobenzene / 4 h / Ambient temperature 2: 95 percent / 85percent hydrazine hydrate / 2-methoxy-ethanol / 2 h / Heating 3: 82 percent / potassium / bis-(2-hydroxy-ethyl) ether / 120 deg C, 10 min then 190-195 deg C, 3h then R.T., overnight
Multi-step reaction with 2 steps 1: AlCl3 / nitrobenzene / 5 °C 2: Zn-Hg, aq. acid
  • 64
  • [ 4100-80-5 ]
  • [ 1590-08-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: aluminium chloride 2: amalgamated zinc; hydrochloric acid 3: concentrated sulfuric acid
Multi-step reaction with 2 steps 1: AlCl3 / CH2Cl2 2: H2, aq. HCl / Pd-C / acetic acid
Multi-step reaction with 3 steps 1: AlCl3 2: H2 / Pd-C 3: polyphosphoric acid
  • 65
  • [ 4100-80-5 ]
  • [ 1590-09-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: AlCl3 / CH2Cl2 2: H2, aq. HCl / Pd-C / acetic acid 3: (i) Ph3CNa, Et2O, (ii) /BRN= 506256/, (iii) KOH, EtOH 4: H2, aq. HCl / Pd-C / acetic acid
  • 66
  • [ 4100-80-5 ]
  • [ 1590-07-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: AlCl3 / CH2Cl2 2: H2, aq. HCl / Pd-C / acetic acid 3: (i) Ph3CNa, Et2O, (ii) /BRN= 506256/, (iii) KOH, EtOH
  • 67
  • [ 4100-80-5 ]
  • [ 1590-06-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AlCl3 / CH2Cl2 2: H2, aq. HCl / Pd-C / acetic acid 3: (i) Ph3CNa, Et2O, (ii) /BRN= 506256/, (iii) KOH, EtOH
  • 68
  • [ 469865-77-8 ]
  • [ 4100-80-5 ]
  • 2-benzyl-2-azabicyclo[2.2.1]hept-7-ylmethyl 5-bromo-2-(3'-methyl-2',5'-dioxopyrrolidin-1'-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid at 80℃; for 12h; 5 EXAMPLE 5 0.190 mmol of 3-methyldihydrofuran-2,5-dione is added to a solution of 0.173 mmol of 2'-benzyl-2'-azabicyclo[2.2.1]hept-7'-ylmethyl 2-amino-5-bromobenzoate, obtained in accordance with Example 3, in 1 ml of acetic acid, and the mixture is heated at 80° C. for 12 hours. The mixture is subjected to conventional work-up, giving 2-benzyl-2-azabicyclo[2.2.1]hept-7-ylmethyl 5-bromo-2-(3'-methyl-2',5'-dioxopyrrolidin-1'-yl)benzoate; ESI 512; salt precipitation using 0.5M HCl solution gives 2-benzyl-2-azabicyclo[2.2.1]hept-7-ylmethyl 5-bromo-2-(3'-methyl-2',5'-dioxopyrrolidin-1'-yl)benzoate hydrochloride.
  • 69
  • [ 372-18-9 ]
  • [ 4100-80-5 ]
  • [ 869673-43-8 ]
  • [ 869673-42-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1,3-Difluorobenzene; 2-methylsuccinic anhydride With aluminum (III) chloride at 50 - 78℃; Stage #2: With hydrogenchloride In water at 0 - 20℃; 103 Add methylsuccinic anhydride (5g, 43.8 mmole) to a stirred suspension of 1,3- difluorobenzene (25g, 219.1 mmole) and aluminum chloride (11.7g, 87.6 mmole), keeping the temperature less than 50°C. Stir the reaction overnight at 50°C and then for 3 days at 78°C. Cool to room temperature and slowly add reaction mixture to a mixture of 3N HCI (40 mL) and ice (40g). Add methylene chloride (80 mL) and separate the organic layer, then extract the aqueous phase with additional methylene chloride (70 mL). Wash the combined organic phase twice with 1 N NaOH solution (80 mL) and then acidify the combined basic wash with 6N HCI. Extract the acidic aqueous phase twice with methylene chloride (100 mL), dry over Na2SO4 and concentrate to obtain product. ESMS 229, tR (min) = 1.57. ¹H-NMRshowed a 4: 1 mixture of isomeric products.
  • 70
  • [ 623578-09-6 ]
  • [ 4100-80-5 ]
  • [ 623578-30-3 ]
YieldReaction ConditionsOperation in experiment
In toluene for 2.5h; Heating / reflux; 34 A stirred mixture of 4- (3-amino-4-fluorobenzyl)-2H- phthalazin-1-one (2.02 g, 7.5 mmol; prepared in a manner similar to that described in Example 23), 3- methyldihydrofuran-2,5-dione (0.856 g, 7.5 mmol) and toluene (100 ml) was heated under reflux for 2.5 hours (for the first 30 minutes of this period, traces of water in the mixture were removed by azeotropic distillation). The resulting solid was collected by filtration from the hot mixture, washed with toluene (20 ml) and dried in vacuo to give N- [2-fluoro-5- (4-oxo-3, 4-dihydrophthalazin-l- ylmethyl) phenyl]-2-methylsuccinamic acid (1.91 g) as an off- white solid, m. pt. 140-144°C; 250 MHz 1H-nmr (d6-DMSO) 6 (ppm): 0.95 (d, 3H) (CH3), 2.2-2. 6 (m, 3H) (-CH2CHMe-), 4.1 (s, 2H) (ArCH2-), 6.9-7. 2 (m, 2H) (2 x ArH), 7.6-7. 9 (m, 4H) (4 x ArH), 8.1 (d, 1H) (ArH), 9.55 (s, 1H) (chain CONH), 12.0 (br s, lH) (C02H), 12.5 (s, 1H) (ring CONH) ; m/z (M+H) + 384, 100% purity.
  • 71
  • [ 4486-29-7 ]
  • [ 4100-80-5 ]
  • [ 119028-62-5 ]
YieldReaction ConditionsOperation in experiment
In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; hexane; dichloromethane; di-isopropyl ether; acetone II Compound of formula I where A=--CH2 --2, R1,R3 =--CH2 --, R2 =R4 =H, R5 =R6 =H, R',R"=oxo, R7 =OH and R8 =CH3 EXAMPLE II Preparation of 4-(5,8-methano-5,6,7,8-tetrahydro-2-naphthyl)-4-oxo-2-methyl butyric acid Compound of formula I where A=--CH2 --2, R1,R3 =--CH2 --, R2 =R4 =H, R5 =R6 =H, R',R"=oxo, R7 =OH and R8 =CH3 To a suspension of 13.33 g (0.1 mole) of anhydrous aluminum chloride in 70 cm3 of dry dichloromethane, stirred at ambient temperature, there is slowly added, over about a 30 minute period, an equimolar solution of 7.11 g (0.05 mole) of 1,4-methano-1,2,3,4-tetrahydronaphthalene and 5.7 g (0.05 mole) of methylsuccinic anhydride in 50 cm3 of dry dichloromethane. At the end of the addition, the reaction mixture is stirred for 1 additional hour at ambient temperature, and it is then poured into 100 cm3 of ice water. The organic phase is decanted and the aqueous phase is again extracted twice with 100 cm3 of dichloromethane. The dichloromethane phases are washed with water, dried on sodium sulfate and then evaporated to dryness. The resulting crude oil is crystallized by trituration in 100 cm3 of tepid hexane. After filtration, the resulting beige solid is recrystallized in 120 cm3 of a 90/10 hexane/acetone mixture, thereby yielding 5.1 g of white crystals which are taken up in 50 cm3 of isopropyl ether, filtered and again recrystallized in 80 cm3 of a 60/40 isopropyl ether/hexane mixture. After drying, 1.7 g of 4-(5,8-methano-5,6,7,8-tetrahydro-2-naphthyl)-4-oxo-2methyl butyric acid in the form of a white solid whose melting point is 148° C. are obtained. The NMR1 H 250 MHz and 13 C spectra conform to the expected structure.
  • 72
  • [ 504-24-5 ]
  • [ 4100-80-5 ]
  • 3-methyl-1-(pyridin-4-yl)-pyrrolidin-2,5-dione [ No CAS ]
  • 3-methyl-1-(4-piperidinyl)-pyrrolidin-2,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 5,5-dimethyl-1,3-cyclohexadiene; water; acetic acid; isopropyl alcohol 13 Example 13 The starting material is prepared as follows: The mixture of 28.5 g of 2-methylsuccinic anhydride, 23.5 g of 4-aminopyridine and 350 ml of xylene is refluxed on a water separator while stirring for 3.5 hours. The hot solution is decanted from some gummy residue, cooled, filtered, the residue suspended in 100 ml of boiling isopropanol and filtered off again, to yield the 3-methyl-1-(4-pyridyl)-pyrrolidin-2,5-dione melting at 119°-120°. The mixture of 34.6 g thereof, 9 g of 10% palladium on carbon and 400 ml of glacial acetic acid is hydrogenated at 110° C. and approximately 1.7 atm. until the theoretical amount of hydrogen has been absorbed. The mixture is filtered, evaporated and the residue taken up in water. The pH of the mixture is adjusted to 9-10 with sodium carbonate and the liberated base extracted with methylene chloride. The extract is dried and evaporated, to yield the 3-methyl-1-(4-piperidinyl)-pyrrolidin-2,5-dione, which is used directly without further purification.
  • 73
  • [ 81075-58-3 ]
  • [ 4100-80-5 ]
  • β-methyl-γ,3-dioxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-butanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
In pyridine 54 β-Methyl-γ,3-dioxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-butanoic acid EXAMPLE 54 β-Methyl-γ,3-dioxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-butanoic acid A mixture of 2-methyl succinic anhydride (1.2 g, 10 mmole) and cis-4-hydroxyproline lactone hydrobromide (2.1 g, 10 mmole) in pyridine (5 ml) is kept at 0° for 1 hour and allowed to warm to room temperature. After an additional hour the mixture is partitioned between ethyl acetate and 1 N HCl. The organic layer is washed with copper sulfate solution to remove traces of pyridine, dried (MgSO4) and concentrated under vacuum to yield β-methyl-γ,3-dioxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-butanoic acid along with an isomer. These were separated by column chromatography.
  • 74
  • [ 180330-54-5 ]
  • [ 4100-80-5 ]
  • [ 52240-20-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In chlorobenzene 13 Preparation of 6-(p-chlorophenyl)-8-methyl-1,2,4-triazolo[4,3-b]pyridazine EXAMPLE 13 Preparation of 6-(p-chlorophenyl)-8-methyl-1,2,4-triazolo[4,3-b]pyridazine To a solution of 114 g. of methylsuccinic anhydride in 400 ml. of chlorobenzene is added carefully 270 g. of aluminum chloride. The mixture is heated to 65° C. for 11/2 hours, is cooled, quenched with ice and concentrated hydrochloric acid and extracted with benzene. The benzene layer is extracted with aqueous sodium bicarbonate. After adjusting the pH of the bicarbonate solution to 6.3, concentrated hydrochloric acid is added slowly over a period of several hours with stirring. At pH 5.7, 78 g. of white crystals are filtered off. Recrystallization of this material from ethanol-water affords 3-(p-chlorobenzoyl)-2-methylpropionic acid as white crystals.
With hydrogenchloride In chlorobenzene 17 Preparation of 6-(p-chlorophenyl)-8-methyl-1,2,4-triazolo[4,3-b]pyridazine EXAMPLE 17 Preparation of 6-(p-chlorophenyl)-8-methyl-1,2,4-triazolo[4,3-b]pyridazine To a solution of 114 g. of methylsuccinic anhydride in 400 ml. of chlorobenzene is added carefully 270 g. of aluminum chloride. The mixture is heated to 65° C. for 11/2 hours, is cooled, quenched with ice and concentrated hydrochloric acid and extracted with benzene. The benzene layer is extracted with aqueous sodium bicarbonate. After adjusting the pH of the bicarbonate solution to 6.3, concentrated hydrochloric acid is added slowly over a period of several hours with stirring. At pH 5.7, 78 g. of white crystals are filtered off. Recrystallization of this material from ethanol-water affords 3-(p-chlorobenzoyl)-2-methylpropionic acid as white crystals.
  • 76
  • ((C6H5)2PCH2CH2P(C6H5)2)NiCH2CH(CH3)COO [ No CAS ]
  • [ 15793-01-8 ]
  • [ 4100-80-5 ]
YieldReaction ConditionsOperation in experiment
96% With carbon monoxide In dichloromethane Schlenk tube contg. CH2Cl2 soln. of nickel complex evacuated and 1 atm of CO introduced; analyzed by GLC, GC-mass, and IR;
  • 77
  • [ 112283-41-7 ]
  • [ 4100-80-5 ]
  • [ 1198168-50-1 ]
YieldReaction ConditionsOperation in experiment
31.06% Stage #1: C12H15NO2; 2-methylsuccinic anhydride With aluminum (III) chloride In nitrobenzene at 20℃; for 48.3333h; Stage #2: With hydrogenchloride In water
  • 78
  • [ 36405-75-1 ]
  • [ 4100-80-5 ]
  • [ 1198168-56-7 ]
YieldReaction ConditionsOperation in experiment
36.18% Stage #1: 2-phenoxy-1-(piperidin-1-yl)ethanone; 2-methylsuccinic anhydride With aluminum (III) chloride In nitrobenzene at 20℃; for 48.3333h; Stage #2: With hydrogenchloride In water
  • 79
  • [ 2065-23-8 ]
  • [ 4100-80-5 ]
  • [ 104435-05-4 ]
YieldReaction ConditionsOperation in experiment
34.61% Stage #1: methyl 2-phenoxyacetate; 2-methylsuccinic anhydride With aluminum (III) chloride In nitrobenzene at 20℃; for 48.3333h; Stage #2: With hydrogenchloride; water
  • 80
  • [ 68000-92-0 ]
  • [ 4100-80-5 ]
  • 4-((R)-1-carboxy-2-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)ethylamino)-3(S)-methyl-4-oxobutanoic acid [ No CAS ]
  • 4-((R)-1-carboxy-2-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)ethylamino)-3(R)-methyl-4-oxobutanoic acid [ No CAS ]
  • 4-((R)-1-carboxy-2-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)ethylamino)-2(R)-methyl-4-oxobutanoic acid [ No CAS ]
  • 4-((R)-1-carboxy-2-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)ethylamino)-2(S)-methyl-4-oxobutanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: trans,trans-farnesyl-L-cysteine; 2-methylsuccinic anhydride With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Stage #2: With hydrogenchloride In dichloromethane 58 In a 100 mL round bottom flask, to a solution of S-trans, trans-farnesyl-L-cysteine (325 mg, 1 mmol) and N-methyl-succinic-anhydride (1 mmol) in CH2Cl2 (10 mL) was added N,N-diisopropyl-ethyl- amine (0.87 mL, 5 mmol). The solution was stirred at room temperature for 2 h. The reaction was quenched by 1 N HCl (10 mL) and the pH was adjusted to -2.0-3.0. The mixture was extracted with ethyl acetate (15 mL x 3). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was further purified by preparative HPLC yielding a 6:4 mixture of regioisomeric compounds, N-22 (the 3-methyl isomer) and N-21 (the 2-methyl isomer), wherein each regioisomer is a 1 :1 ratio mixture of R-R and S-R isomers, similar to the regioisomeric mixture of compounds N-34 and N-33 in Example 41 (296 mg, 67% yield). 1H-NMR (500 MHz, CDCl3): δ 1.14-1.24 (m, 3H), 1.53 (s, 6H), 1.59 (s, 3H), 1.61 (s, 3H), 1.88-2.03 (m, 8H), 2.29-2.66 (m, 2H), 2.72-3.01 (m, 3H), 3.07-3.16 (m, 2H), 4.59 (dd, J = 5.0, 10.0 Hz, 0.5H), 4.69 (dd, J = 5.0, 10.0 Hz, 0.5H), 5.01 (m, 2H), 5.13 (dd, J = 5.0, 15.0 Hz, IH), 6.52 (m, 0.5H), 6.70 (m, 0.5H), 8.80 (broad, 2H). 13C-NMR (125 MHz, CDCl3): δ 15.00, 15.12, 15.56, 15.82, 15.98, 16.51, 16.69, 16.84, 24.71, 25.36, 25.39, 25.50, 25.67, 28.74, 28.79, 31.42, 31.47, 31.53, 31.72, 35.04, 35.48, 35.61, 36.59, 36.98, 37.64, 38.40, 38.60, 38.67, 50.50, 50.65, 50.95, 51.02, 117.90, 118.26, 118.29, 122.64, 122.67, 122.71, 123.27, 130.30, 130.35, 134.34, 134.38, 139.26, 139.27,139.29, 139.33, 170.86, 171.02, 174.01, 174.84, 174.96, 175.23, 175.40, 175.76, 177.16, 179.36, 180.65; ES- MS: mass calcd for Chemical Formula: C23H37NO5S 439.61. Found (M+) m/z 440.3, (M+Na) m/z 462.3.
  • 81
  • [ 107-11-9 ]
  • [ 4100-80-5 ]
  • [ 1220986-03-7 ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: 1-amino-2-propene; 2-methylsuccinic anhydride In dichloromethane at 20℃; for 12h; Stage #2: With 1,1'-carbonyldiimidazole In dichloromethane for 0.5h; Reflux;
  • 82
  • C39H41N3O5 [ No CAS ]
  • [ 4100-80-5 ]
  • (S)-{{2-[1-(2-Benzoylphenyl)amino]-2-{4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}propyl}}-aminocarbonyl-(2-methyl)-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% Stage #1: C39H41N3O5 With hydrogenchloride In 1,4-dioxane at 20℃; for 1h; Inert atmosphere; Stage #2: 2-methylsuccinic anhydride With dmap In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;
  • 83
  • [ 97-65-4 ]
  • dihydro-4-methyl-2(3H)-furanone [ No CAS ]
  • [ 1679-47-6 ]
  • [ 4100-80-5 ]
YieldReaction ConditionsOperation in experiment
1: 30% 2: 44% 3: 25% With 5% active carbon-supported ruthenium; hydrogen at 150℃;
  • 84
  • rac-benzyl cis,cis-9-(cyclopropylamino)-1,2,3,3a,9,9a-hexahydro-4H-cyclopenta[b]quinoline-4-carboxylate [ No CAS ]
  • [ 4100-80-5 ]
  • rac-4-[{cis,cis-4-[(benzyloxy)carbonyl]-1,2,3,3,9,9a-hexahydro-1H-cyclopenta[b]quinolin-9-yl}(cyclopropyl)amino]-2-methyl-4-oxobutanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane at 110 - 130℃; for 2h; Sealed tube; 10 Example 10: Preparation of Racemic 4-[{cis, cis-4-[(Benzyloxy)carbonyl]-2,3)3 )9,9a- hexahydro-lH-cyclopenta[b]quinolin-9-yl}(cyclopropyl)amino]-2-methyl-4-oxobutanoic acid (10); 10[00217] A solution of racemic benzyl cis, cis-9-(cyclopropylamino)-l,2,3,3a,9,9a- hexahydro-4H-cyclopenta[6]quinoline-4-carboxylate (IE) (25 mg, 0.069 mmol, 1 equiv) and 3- methyldihydrofuran-2,5-dione (0.15 mL, 1.6 mmol, 23 equiv) in dioxane (0.35 mL) was heated to 110 °C in a sealed tube. After heating for 1 h, the oil bath temperature was increased to 130 °C for 1 h. The reaction mixture was then cooled to 23 °C and partitioned between ethyl acetate and aqueous hydrochloric acid solution. The organic layer was washed with saturated aqueous sodium chloride solution, and the washed solution was dried over sodium sulfate. The dried solution was filtered, and the filtrate was concentrated. The residue was purified by flash- column chromatography (dichloromethane, grading to 10% methanol-dichloromethane). The residue was then dissolved in DMSO (1 mL), and purified by reverse-phase HPLC (40% acetonitrile- water, grading to 80% acetonitrile- water, with 0.1% trifluoroacetic acid in both the acetonitrile and water) to afford 10. [M+H]+: 477.2.
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 4100-80-5 ]

Anhydrides

Chemical Structure| 17347-61-4

[ 17347-61-4 ]

2,2-Dimethylsuccinicanhydride

Similarity: 0.97

Chemical Structure| 5617-74-3

[ 5617-74-3 ]

3-Oxabicyclo[3.1.0]hexane-2,4-dione

Similarity: 0.90

Chemical Structure| 14166-28-0

[ 14166-28-0 ]

(3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione

Similarity: 0.90

Chemical Structure| 67911-21-1

[ 67911-21-1 ]

6,6-Dimethyl-3-oxabicyclo[3.1.0]hexane-2,4-dione

Similarity: 0.88

Chemical Structure| 108-30-5

[ 108-30-5 ]

Dihydrofuran-2,5-dione

Similarity: 0.86

Esters

Chemical Structure| 17347-61-4

[ 17347-61-4 ]

2,2-Dimethylsuccinicanhydride

Similarity: 0.97

Chemical Structure| 1679-47-6

[ 1679-47-6 ]

3-Methyldihydrofuran-2(3H)-one

Similarity: 0.96

Chemical Structure| 7452-79-1

[ 7452-79-1 ]

Ethyl 2-methylbutanoate

Similarity: 0.93

Chemical Structure| 5617-74-3

[ 5617-74-3 ]

3-Oxabicyclo[3.1.0]hexane-2,4-dione

Similarity: 0.90

Chemical Structure| 14166-28-0

[ 14166-28-0 ]

(3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione

Similarity: 0.90

Related Parent Nucleus of
[ 4100-80-5 ]

Aliphatic Heterocycles

Chemical Structure| 17347-61-4

[ 17347-61-4 ]

2,2-Dimethylsuccinicanhydride

Similarity: 0.97

Chemical Structure| 1679-47-6

[ 1679-47-6 ]

3-Methyldihydrofuran-2(3H)-one

Similarity: 0.96

Chemical Structure| 5617-74-3

[ 5617-74-3 ]

3-Oxabicyclo[3.1.0]hexane-2,4-dione

Similarity: 0.90

Chemical Structure| 14166-28-0

[ 14166-28-0 ]

(3aR,4S,7R,7aS)-rel-Hexahydro-4,7-methanoisobenzofuran-1,3-dione

Similarity: 0.90

Chemical Structure| 63095-51-2

[ 63095-51-2 ]

(R)-4-Propyldihydrofuran-2(3H)-one

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Tetrahydrofurans

Chemical Structure| 17347-61-4

[ 17347-61-4 ]

2,2-Dimethylsuccinicanhydride

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Chemical Structure| 1679-47-6

[ 1679-47-6 ]

3-Methyldihydrofuran-2(3H)-one

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Chemical Structure| 63095-51-2

[ 63095-51-2 ]

(R)-4-Propyldihydrofuran-2(3H)-one

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Chemical Structure| 19406-00-9

[ 19406-00-9 ]

Methyl 2-oxotetrahydrofuran-3-carboxylate

Similarity: 0.87

Chemical Structure| 77513-58-7

[ 77513-58-7 ]

Ethyl 2-oxotetrahydrofuran-3-carboxylate

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