57595-23-0|Methyl 4-oxotetrahydrofuran-3-carboxylate| Ambeed

Structure of 57595-23-0

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Quality Control of [ 57595-23-0 ] Purity: 96% SDS Specification

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Product Details of [ 57595-23-0 ]

CAS No. :	57595-23-0
Formula :	C₆H₈O₄
M.W :	144.13
SMILES Code :	COC(=O)C1COCC1=O
MDL No. :	MFCD19707049
InChI Key :	FCUDJBUBWCJOLK-UHFFFAOYSA-N
Pubchem ID :	14666564

Safety of [ 57595-23-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 57595-23-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	0
Fraction Csp3	0.67
Num. rotatable bonds	2
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	31.41
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	52.6 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.3
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	-0.25
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.63
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-0.96
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.66
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.02

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.44
Solubility	51.8 mg/ml ; 0.36 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-0.4
Solubility	57.9 mg/ml ; 0.401 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.44
Solubility	52.2 mg/ml ; 0.362 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.36 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.47

Application In Synthesis of [ 57595-23-0 ]

* 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 [ 57595-23-0 ]

[ 57595-23-0 ] Synthesis Path-Downstream 1~35

1
[ 96-35-5 ]
[ 292638-85-8 ]
[ 57595-23-0 ]

Yield	Reaction Conditions	Operation in experiment
24%		To a stirred slurry of sodium hydride (2.2 g, 55 mmol) in dry ether (40 mL) at room temperature (rt) was added methyl glycolate (4.5 g, 50 mmol) dropwise. The reaction mixture was stirred for 14 h, then it was concentrated under vacuo. To the solid was added methyl acrylate (5.2 g, 55 mmol) in DMSO (20 mL) at O0C and the mixture was stirred for 15 min, and the cool bath was removed and it was stirred for 45 min. The mixture was poured into 5% H2SO4 (60 mL), and it was extracted with ether (150 mL). The organic layer was dried, concentrated and purified by column chromatography to give 1.7 g (24%) of the title compound. 1H NMR (CDCl3): 4.51-4.40 (m, 2H), 4.03 (q, J = 8.1 Hz, 2H), 3.80 (s, 3H), 3.54 (t, J = 8.1 Hz, IH).
4.5 g (31%)	With sodium; In dimethyl sulfoxide;	Synthesis of 2,5-dihydro furan 3,4-dicarboxylic acid 2.3 g (0.1 mol) sodium was pulverized under toluene and the solvent was replaced with 75 ml ether. 11 ml (0.1 mol) methylglycolate was added to the mixture under stirring until the evolution of hydrogen gas had ceased. To the dry sodium derivative remaining after destination of the ether, a solution of 10 ml (0.12 mol) distilled methylacrylate in 50 ml DMSO was added while the reaction was kept at 4 C. After 15 minutes the solution was stirred for an additional 30-40 min at room temperature and poured into aqueous H2SO4 at 4 C. and extracted with ether. Washing of the organic layer with a saturated NaCl solution, drying over NaSO4 and removal of the ether was followed by destination under reduced pressure to give 4.5 g (31%) of 4-oxo-tetrahydro furane 3-carboxylic acidmethyl ester.
		To a suspension of NaH (185 g, 4.6 mol, 60% weight) in THF (4 L) was charged methyl 2-hydroxyacetate (380 g, 4.2 mol) dropwise at 0 C. After the addition, the reaction mixture was stirred for 30 mm at ambient temperature and then re-cooled to 0 C. A solution of methylacrylate (400 g, 4.64 mol) in DMSO (2 L) was added dropwise over 2 hours at 0 C. The resulting reaction mixture was stirred for 30 mm at 0 C and for 2 h at 20 C. After TLC showed that the start material was consumed completely, the mixture was quenched with 1.5 L of 5% H2S04 (slowly) and extracted with EtOAc (3 L). The combined organic layers were washed with brine (1 L), dried over Na2SO4, filtered and concentrated to afford Methyl 4-oxotetrahydrofuran-3-carboxylate (11) as a liquid. The crude oil was used in the next step without further purification. ?H NMR (CDC13, 400 MHz) : 4.3 5-4.45 (m, 2H), 3.86-3.97 (m, 2H), 3.72 (s, 3H), 3.47 (t, 1H).

To a suspension of NaH (185 g, 4.6 mol, 60 weight) in T HF (4 L) was charged methyl 2-hydroxyacetate (380 g, 4.2 mol) dropwise at 0 . After the addition, the reaction mixture was stirred for 30 min at ambient temperature and then re-cooled to 0 . A solution of methyl acrylate (400 g, 4.64 mol) in DMSO (2 L) was added dropwise over 2 hours at 0 . The resulting reaction mixture was stirred for 30 min at 0 and for 2 h at 20 . After TLC showed that the start material was consumed completely, the mixture was quenched with 1.5 L of 5 H2SO4(slowly) and extracted with EtOAc (3 L) . The combined organic layers were washed with brine (1 L) , dried over Na2SO4, filtered and concentrated to afford Methyl 4-oxotetrahydrofuran-3-carboxylate (11) as a liquid. The crude oil was used in the next step without further purification.1H NMR (CDCl3, 400 MHz) delta: 4.35-4.45 (m, 2H) , 3.86-3.97 (m, 2H) , 3.72 (s, 3H) , 3.47 (t, 1H) .

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 2124 - 2130.
[2]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 754 - 760.
[3]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1124 - 1130.
[4]Patent: WO2008/21456,2008,A2 .Location in patent: Page/Page column 32.
[5]Patent: WO2018/137573,2018,A1 .Location in patent: Page/Page column 104.
[6]Tetrahedron Letters,1989,vol. 30,p. 6129 - 6132.
[7]Tetrahedron,1991,vol. 47,p. 4847 - 4860.
[8]Patent: US2003/203951,2003,A1 .
[9]Patent: WO2016/49100,2016,A1 .Location in patent: Page/Page column 22; 23.
[10]Patent: WO2016/45126,2016,A1 .Location in patent: Page/Page column 20.
[11]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1193 - 1198.

2
[ 57595-23-0 ]
[ 62-53-3 ]
[ 127956-17-6 ]

References: [1]Tetrahedron Letters,1989,vol. 30,p. 6129 - 6132.
[2]Tetrahedron,1991,vol. 47,p. 4847 - 4860.

4
[ 57595-23-0 ]
[ 1073-69-4 ]
4-[(4-chloro-phenyl)-hydrazono]-tetrahydro-furan-3-carboxylic acid methyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2591 - 2594.

5
[ 57595-23-0 ]
[ 143-33-9 ]
[ 867288-07-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4854 - 4857.

6
[ 57595-23-0 ]
[ 260967-07-5 ]
benzyl 1-(3-(methoxycarbonyl)-tetrahydro-4-oxofuran-3-yl)-3-phenylpropylcarbamate [ No CAS ]

References: [1]Organic Letters,2006,vol. 8,p. 4923 - 4925.

7
[ 57595-23-0 ]
[ 2986-19-8 ]
[ 150787-18-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In water; at 20℃; for 6.08333h;Heating / reflux;	To a stirred solution of potassium hydroxide (1.97 g, 31.7 mmol) and 2-methyl-2- thiopseudourea sulfate (4.41 g, 31.7 mmol) in water (15 mL) was added dropwise of methyl tetrahydro-4-oxofuran-3-carboxylate (1.59 g, 15.9 mmol) over 5 min. The mixture was stirred at rt for 3 h and refluxed for 3 h. It was evaporated to dryness to give 4.1 g of crude product and used for next reaction without further purification.

References: [1]Patent: WO2008/21456,2008,A2 .Location in patent: Page/Page column 32.

8
[ 57595-23-0 ]
4-(3-fluoro-3'-methoxy-biphenyl-4-ylcarbamoyl)-2,5-dihydro-furan-3-carboxylic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4854 - 4857.

9
[ 57595-23-0 ]
4-[3-chloro-4-(2-chloro-6-fluoro-benzyloxy)-phenylcarbamoyl]-2,5-dihydro-furan-3-carboxylic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4854 - 4857.

10
[ 57595-23-0 ]
4-(3,5-difluoro-3'-trifluoromethoxy-biphenyl-4-ylcarbamoyl)-2,5-dihydro-furan-3-carboxylic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4854 - 4857.

11
[ 57595-23-0 ]
4-(2,3,5,6-tetrafluoro-3'-trifluoromethoxy-biphenyl-4-ylcarbamoyl)-2,5-dihydro-furan-3-carboxylic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4854 - 4857.

12
[ 57595-23-0 ]
[ 57595-24-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4854 - 4857.

13
[ 57595-23-0 ]
[ 57595-25-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4854 - 4857.

14
[ 57595-23-0 ]
[ 38983-99-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2591 - 2594.

15
[ 57595-23-0 ]
[ 127956-19-8 ]

References: [1]Tetrahedron,1991,vol. 47,p. 4847 - 4860.
[2]Tetrahedron Letters,1989,vol. 30,p. 6129 - 6132.

16
[ 57595-23-0 ]
5-[(Z)-Phenylimino]-tetrahydro-pyran-3-carboxylic acid methyl ester [ No CAS ]

References: [1]Tetrahedron,1991,vol. 47,p. 4847 - 4860.

17
[ 57595-23-0 ]
[ 127956-18-7 ]

References: [1]Tetrahedron,1991,vol. 47,p. 4847 - 4860.

18
[ 57595-23-0 ]
[ 127956-18-7 ]

References: [1]Tetrahedron Letters,1989,vol. 30,p. 6129 - 6132.

19
[ 292638-85-8 ]
[ 57595-23-0 ]

Yield	Reaction Conditions	Operation in experiment
54%		To a suspension of NaH (6.66g, 166.5 mmol) in ether (500 mL) add methyl glycolate (15.0 g, 166.5 mmol) drop wise. Stir the reaction until evolution of H2 gas ceases. Concentrate and dissolve the solid in DMSO (300 mL). Cool the reaction to 0 oC and add methyl acrylate (16.6 mL, 183.17 mmol) drop wise. Warm the reaction to room temperature and stir overnight. Acidify the reaction with 10% HCl and extract with ether (3X). Combine organic extracts and wash with brine. Dry the organic solution (NA2SO4), filter, and concentrate in vacuo. Purify by flash chromatography (250 g SI02, 40 ML/MIN, 0-50% ethyl acetate/hexane for 20 minutes and then 50% ethyl acetate/hexane for 13 minutes) to yield 4-oxo-tetrahydro-furan-3-carboxylic acid methyl ester 4a (12.9g, 89.2 mmol, 54%) as a colorless OIL. 1H NMR (8, 400 MHz, CDCL3) : 4.50 (dd, 1H, J=8.4, 9.6 Hz), 4.46 (dd, 1H, J=8.4, 9.6 Hz), 4. 05 (d, 1H, J=16.8 Hz), 3.79, (s, 3H), 3.97 (d, 1H, J=16.8, Hz), 3.54 (t, 1H, J=8.4Hz). MS calcd. 144; found (EI) 144.

References: [1]Patent: WO2004/94400,2004,A2 .Location in patent: Page 40.

20
[ 57595-23-0 ]
[ 57-13-6 ]
[ 848398-40-3 ]

Yield	Reaction Conditions	Operation in experiment
		Example 1 5,7-dihydrofuro[3,4-d]pyrimidine-2,4(1H,3H)-dione: To Methyl 4-oxotetrahydrofuran-3-carboxylate (18.30 g), urea (11.44 g), methanol (100 mL) and concentrated hydrochloric acid (5 mL) were added. The mixture was refluxed with heating for two hours. The obtained suspension was stirred for 15 minutes in an ice-bath. The precipitate was filtered under reduced pressure, and washed with water (20 mL x 2 times). 2 mol/L aqueous solution of sodium hydroxide (100 mL) and water (30 mL) were added to the obtained precipitate. The mixture was refluxed with heating for 1 hour. Concentrated hydrochloric acid was dropped to the reaction solution in an ice-bath. The precipitate was filtered under reduced pressure, and then the precipitate was washed with water and acetone, dried under reduced pressure to give the title compound (15.7 g) having the following physical data. TLC: Rf 0.32 (methanol: ethyl acetate = 10 : 1); 1H-NMR (300MHz, DMSO-d6). delta 11.23, 11.44-11.10, 11.00, 4.70.

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 2124 - 2130.
[2]Patent: EP1666468,2006,A1 .Location in patent: Page/Page column 32.

21
[ 623-50-7 ]
[ 292638-85-8 ]
[ 57595-23-0 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether; dimethyl sulfoxide; at 0 - 20℃; for 1.75h;	EXAMPLE 13; 4-Oxo-tetrahydro-furan-3-carboxylic acid methyl ester. To a stirred slurry of sodium hydride (1.67 g, 60% in mineral oil, 44.0 mmol) in dried ether was added with ethyl glycolate, dropwise over 15 minutes. The reaction was warmed up to room temperature for 30 min while stirring and concentrated in vacuo to provide white solid. The solid was treated with methyl acrylate (4.16 g, 49 mmol) in DMSO (20 mL) at 0 C. for 15 minutes and room temperature for 45 minutes. The mixture was poured into 5% H2SO4 and extracted with ethyl acetate. Organic layer was washed with brine, dried over Mg2SO4 and concentrated to give 4-oxo-tetrahydro-furan-3-carboxylic acid methyl ester as a colorless oil. MS (ES): [M-1]- cal'cd for C6H7O3, 143; found: 143.

References: [1]Patent: US2006/9451,2006,A1 .Location in patent: Page/Page column 19.

22
[ 57595-23-0 ]
4-cyano-tetrahydro furane 3-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium cyanide; sulfuric acid; In water;	To a stirred solution of 3.9 g (60 mmol) KCN in 5.5 ml of water at 4 C., a solution of 2.9 g (20 mmol) of 4-oxo-tetrahydro furane 3-carboxylic acid methyl ester in ether (26 ml) was added. To the precipitate of salts, 3.5 ml H2SO4 (18 N) was added and stirred for 16 hours. Then the organic solution was separated, the salts were washed twice with benzene, dried over sodium sulfate and concentrated in vacuo to give 4-cyano-tetrahydro furane 3-carboxylic acid methyl ester.

References: [1]Patent: US2003/203951,2003,A1 .

23
[ 57595-23-0 ]
[ 1025373-45-8 ]
[ 7087-68-5 ]
[ 177734-77-9 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	3-(Trifluoromethylsulfonyloxy)-2,5-dihydrofuran-4-carboxylic acid methyl ester A solution of <strong>[57595-23-0]tetrahydrofuran-3-one-4-carboxylic acid-methyl ester</strong> (P. Dowd, S.-C. Choi, Tetrahedron 1991, 47, 4847) (2.88 g, 20 mmol) in dichloromethane (200 ml) is mixed at -78 C. with diisopropyl(ethyl)amine (3.96 ml, 23.2 mmol). After 10 minutes, trifluoromethanesulfonic acid anhydride (3.88 ml, 23.2 mmol) is slowly added in drops to it. The batch is warmed to room temperature, stirred for 2 hours and concentrated by evaporation. The residue is purified by column chromatography (SiO2) with ethyl acetate-hexane: 3.62 g (66%) of product. 1H-NMR (CDCl3): delta=3.85 (s, 3H), 4.80 (t, 2H), 4.92 (t, 2H).

References: [1]Patent: US6391887,2002,B1 .

24
[ 158001-24-2 ]
[ 5417-82-3 ]
[ 57595-23-0 ]
[ 158001-25-3 ]

Yield	Reaction Conditions	Operation in experiment
4.7 g (54%)	With sodium methylate; In ethanol;	(e) 1-(3-Tetrahydrofuranyl)-3-methyl-5-amino-1H-pyrazole-4-carbonitrile A mixture of 3-tetrahydrofuranylhydrazine hydrochloride (6.2 g, 0.045 mol), sodium methoxide (2.4 g, 0.045 mol) and ethanol (70 ml) was refluxed under argon for 10 minutes. The reaction mixture was cooled to room temperature and 1-ethoxyethylidene malononitrile (6.1 g, 0.045 mol) was added. The reaction mixture was heated to reflux and stirred for 21 hours. The reaction was cooled and the solvent was removed in vacuo. The residue was recrystallized from water to afford 4.7 g (54%) of 1-(3-tetrahydrofuranyl)-3-methyl-5-amino-1H-pyrazole-4-carbonitrile as yellow crystals, m.p. 134-135 C. when dried at 90 C. in high vacuum.

References: [1]Patent: US5294612,1994,A .

25
[ 57595-23-0 ]
[ 22929-52-8 ]

Yield	Reaction Conditions	Operation in experiment
6.8 g (79%)	In sulfuric acid;	(b) Tetrahydrofuran-3-one A solution of <strong>[57595-23-0]methyl 3-oxo-tetrahydrofuranyl-4-carboxylate</strong> (14.5 g, 0.1 mol) in 10percent H2 SO4 (50 ml) was refluxed for 1 hour. The reaction mixture was cooled and extracted with ether (3*100 ml). The organic layers were combined, dried over MgSO4 and concentrated in vacuo. The pale gold residue was distilled to afford 6.8 g (79percent) of tetrahydrofuran-3-one, B.P. 74°-75° C. at 100 mm Hg.

References: [1]Patent: US5294612,1994,A .

26
[ 674793-32-9 ]
[ 57595-23-0 ]
[ 773140-30-0 ]

Yield	Reaction Conditions	Operation in experiment
30%	In ethanol; at 80℃;	To a suspension of 4-oxo-tetrahydroiuran-3-carboxylic acid methyl ester (prepared according to Dowd, P.; Choi, S-C. Tetrahedron, 1991, 47, 4847-4860; 800 mg, EPO <DP n="60"/>5.55 mmol, leq) in ethanol (20 ml) was added a solution of 2-fluoro-5-chloro- benzamidine (961 mg, 5.55 mmol, 1 eq) in EtOH (10 ml). The reaction mixture was heated to 80C overnight. The reaction mixture was cooled to r.t. and the white precipitate was filtered and washed with cold ethyl actetate (2 x 20 ml). The crude residue was partitioned between chloroform and water. The aqueous layer was acidified to pH 4 and the product was extracted with chloroform (3 x 50 ml). The organic layers were combined, washed with brine, dried over MgSO4, filtered and concentrated in vacuo to give a crude solid which was purified by flash column chromatography (5% MeOH in EtOAc) to give a white solid 2-(5-chloro-2-fluoro- phenyl)-5,7-dihydrofuro[3,4-d]pyrimidin-4-ol (440mg, 30%)

References: [1]Patent: WO2006/35061,2006,A1 .Location in patent: Page/Page column 58; 59.

27
[ 57595-23-0 ]
[ 1071-37-0 ]
[ 864439-11-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In water; at 20 - 80℃; for 25.5h;	To a solution of ethyl imidothiocarbamate hydrobromide (2,59 g) in water (25 mL) were added sodium carbonate (1.48 g) and methyl 4-oxotetrahydro-3-furancarboxylate (1.44 g), then the mixture was stirred for 3.5 hours at room temperature, 18 hours at 70C, then 4 hours at 80C. The reaction mixture was cooled to room temperature, the precipitate was collected, washed with water and diisopropyl ether sequentially to give the title compound (744 mg) having the following physical data. The former water layer was washed with ethyl acetate, extracted with dichloromethane. The organic layer was washed with brine, dried over anhydrous sodium sulfate, concentrated. The obtained residue was added by diisopropyl ether, the precipitated solid was collected to give the title compound (139 mg) having the following physical data. TLC: Rf0.65 (ethyl acetate); 1H NMR (CDCl3): delta 1.38 (t, J = 7.36 Hz, 3 H), 3.20 (q, J = 7.36 Hz, 2 H), 4.80 - 4.97 (m, 2 H), 4.98 - 5.15 (m, 2 H), 11.62 - 12.25 (m, 1 H).

References: [1]Patent: EP1724264,2006,A1 .Location in patent: Page/Page column 70.

28
[ 57595-23-0 ]
[ 3886-69-9 ]
[ 362488-78-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 694 - 699.

29
[ 57595-23-0 ]
[ 358-23-6 ]
[ 177734-77-9 ]

Yield	Reaction Conditions	Operation in experiment
		Sodium hydride (4 g, 60% w/w in oil dispersion, 100 mmol) was added to a flame-dried flask along with ether (100 mL). To the reaction flask under nitrogen atmosphere, methyl glycolate (7.7 mL, 100 mmol) was added slowly with constant stirring. The reaction mixture was allowed to stir at room temperature for 2 hours under nitrogen atmosphere then solvent was removed in vacuo. To the residue, methyl acrylate (10.8 mL, 120 mmol) in DMSO (50 mL) was added in one portion while the reaction flask was kept immersed in an ice bath. The reaction mixture was allowed to stir at 0 C for 15 minutes then at room temperature for 1 hour. The reaction mixture was then filtered through Celte'3', poured into ice-cold aqueous sulfuric acid solution (150 mL, 2N), and extracted with ether (2 x 200 mL). The organic layer was washed with saturated NaCl solution (500 mL), dried over anhydrous Na2S04, filtered, and solvent was removed in vacuo. The intermediate ketoester was recovered in 26% yield (3.7 g, 25.7 mmol) afterpurificationby column chromatography on silica using 25% ethyl acetate/hexanes as the eluent (Rf= 0.3). The ketoester intermediate (3.7g, 25.7 mmol) was added slowly to a solution of sodium hydride (1.4 g, 60% w/w in oil dispersion, 34 mmol) in ether (80 mL) at 0 C with constant stirring under nitrogen atmosphere. After 30 minutes, trifluoromethanesulfonic anhydride (5.3 mL, 31.4 mmol) was added dropwise over 5 minutes. The reaction mixture was allowed to stir at 0 C for an additional 1.5 hours then the reaction was poured into water (80 mL) and the layers were separated. The aqueous phase was washed with dichloromethane (2 x 60 mL) and the organic phases were combined. The organic layer was dried over anhydrous Na2SO4, filtered, and solvent was removed in vacuo. The 2,5- dihydrofuran ester 13a was recovered in 23% yield (1.6 g, 5.8 mmol) after purification by column chromatography on silica using 25% ethyl acetate/hexanes as the eluent (Rf= 0.45). MS: calc. for C7H7F306S : 257.9 ; Found: GC-MS 7nl5 275 (MH).
		To a solution of DIEA (860 mI_, 4.99 mmol) in dry DCM (20 ml_) cooled to -78C under Argon was added a solution of methyl 4-oxotetrahydrofuran-3- carboxylate (628 mg, 4.63 mmol in 20 ml_ DCM) dropwise. The reaction mixture was stirred -78C for 30 minutes post addition and then treated dropwise with neat trifluoromethanesulfonic anhydride (820 mI_, 4.98 mmol). After stirring the reaction mixture for 2 h 0C, the reaction mixture was quenched by the cautious addition of cold water (11 ml_). The reaction mixture was warmed to ambient temperature and diluted with water and diethyl ether. The aqueous layer was extracted with diethyl ether and the combined organic layers washed with sat. NaHCC>3 and brine, then dried over MgS04. The resulting residue was concentrated in vacuo followed by flash chromatography (Si02, 0-50% DCM/heptane) to yield a pale yellow oil.

References: [1]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 754 - 760.
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1124 - 1130.
[3]Patent: WO2005/40109,2005,A1 .Location in patent: Page/Page column 78-79.
[4]Patent: WO2019/171278,2019,A1 .Location in patent: Page/Page column 122.

30
[ 67-56-1 ]
[ 78-85-3 ]
[ 57595-23-0 ]
C₁₁H₁₈O₆ [ No CAS ]

References: [1]Chemistry - A European Journal,2008,vol. 14,p. 3078 - 3092.

31
[ 67-56-1 ]
[ 57595-23-0 ]
[ 107-02-8 ]
C₁₀H₁₆O₆ [ No CAS ]

References: [1]Chemistry - A European Journal,2008,vol. 14,p. 3078 - 3092.

32
[ 67-56-1 ]
[ 57595-23-0 ]
[ 123-73-9 ]
C₁₁H₁₈O₆ [ No CAS ]

References: [1]Chemistry - A European Journal,2008,vol. 14,p. 3078 - 3092.

33
[ 798541-68-1 ]
[ 96-35-5 ]
[ 57595-23-0 ]

Yield	Reaction Conditions	Operation in experiment
26%		Sodium hydride (4 g, 60% w/w in oil dispersion, 100 mmol) was added to a flame-dried flask along with ether (100 mL). To the reaction flask under nitrogen atmosphere, methyl glycolate (7.7 mL, 100 mmol) was added slowly with constant stirring. The reaction mixture was allowed to stir at room temperature for 2 hours under nitrogen atmosphere then solvent was removed in vacuo. To the residue, methyl acrylate (10.8 mL, 120 mmol) in DMSO (50 mL) was added in one portion while the reaction flask was kept immersed in an ice bath. The reaction mixture was allowed to stir at 0 C for 15 minutes then at room temperature for 1 hour. The reaction mixture was then filtered through Celte'3', poured into ice-cold aqueous sulfuric acid solution (150 mL, 2N), and extracted with ether (2 x 200 mL). The organic layer was washed with saturated NaCl solution (500 mL), dried over anhydrous Na2S04, filtered, and solvent was removed in vacuo. The intermediate ketoester was recovered in 26% yield (3.7 g, 25.7 mmol) afterpurificationby column chromatography on silica using 25% ethyl acetate/hexanes as the eluent (Rf= 0.3). The ketoester intermediate (3.7g, 25.7 mmol) was added slowly to a solution of sodium hydride (1.4 g, 60% w/w in oil dispersion, 34 mmol) in ether (80 mL) at 0 C with constant stirring under nitrogen atmosphere. After 30 minutes, trifluoromethanesulfonic anhydride (5.3 mL, 31.4 mmol) was added dropwise over 5 minutes. The reaction mixture was allowed to stir at 0 C for an additional 1.5 hours then the reaction was poured into water (80 mL) and the layers were separated. The aqueous phase was washed with dichloromethane (2 x 60 mL) and the organic phases were combined. The organic layer was dried over anhydrous Na2SO4, filtered, and solvent was removed in vacuo. The 2,5- dihydrofuran ester 13a was recovered in 23% yield (1.6 g, 5.8 mmol) after purification by column chromatography on silica using 25% ethyl acetate/hexanes as the eluent (Rf= 0.45). MS: calc. for C7H7F306S : 257.9 ; Found: GC-MS 7nl5 275 (MH).

References: [1]Patent: WO2005/40109,2005,A1 .Location in patent: Page/Page column 78-79.

34
[ 57595-23-0 ]
[ 3959-07-7 ]
[ 1186091-01-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;acetic acid; In ethanol; for 2h;Reflux;	To a solution of methyi-4-oxo-tetrahydrofuro-3-carboxylate (1.0 g, 6.94 mmol) in ethanol (16 niL) was added 4-bromobenzylamme (1.621 g5 7.29 mmol) followed by triethylamine (0.919 niL, 6.59 mmol) and acetic acid (0.119 mL, 2.082 mmol). The mixture was refluxed for 2 h. The mixture was concentrated in vacuo, taken up in EtOAc (30 mL) and water (30 mL). The <n="35"/>organic layer was then washed with saturated NaHCC>3 (20 mL). The aqueous layer was then extracted with EtOAc (3 x 40 mL) and the combined organic extracts were washed with water (30 mL) and brine (30 mL), dried over Na2SC>4 and concentrated in vacuo to give a brown oil which solidified over time to an oily brown solid, which was taken on crude to the next reaction.

References: [1]Patent: WO2009/108496,2009,A1 .Location in patent: Page/Page column 33-34.

35
[ 57595-23-0 ]
[ 29198-41-2 ]
[ 1186090-97-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;acetic acid; In ethanol; for 6h;Reflux;	To a solution of metliyl-4-oxo-tetrahydrofuro-3-carboxylate (1.18 g, 8,19 mmol) in ethanol (5 mL), l-(l,3-benzothiazol-2~yl)methanamine hydrochloride (1.73 g, 8.60 ramol), triethylamine (1.20 mL, 8.60 mmol) and acetic acid (47 muL, 0.819 mmol) were added and the reaction mixture was heated to reflux for 6 hr, cooled to ambient temperature and concentrated in vacuo. The resultant residue was partitioned between EtOAc (10 mL) and H2O (5 mL) and the organic layer was washed with KHSO4 (1 X 5 mL), NaHCO3 (1 X 5 mL) brine (1 X 5 mL), dried over MgSO4, filtered and concentrated in vacuo. Purification by flash chromatography 10,15% EtOAc/hexanes on SiO2 (40 S+ column) afforded 610 mg of an orange foam: * H NMR (500 MHz, CDCl3) delta 3.73 (s, 3 H), 4.67 (d, 2 H, J- 6.8 Hz), 4.80 (s, 4 H), 7.40 (t, 1 H, J= 7.5Hz), 7.50 (I, 1 H, J= 12 Hz), 7.87 (d, 1 H, J= 8.0 Hz), 7.99 (d, 1 H, J= 8.2 Hz).

References: [1]Patent: WO2009/108496,2009,A1 .Location in patent: Page/Page column 24-25.

Historical Records

Technical Information

• Acyl Group Substitution • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bouveault-Blanc Reduction • Bucherer-Bergs Reaction • Catalytic Hydrogenation • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Ester Cleavage • Fischer Indole Synthesis • Grignard Reaction • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions with Organometallic Reagents • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Related Functional Groups of
[ 57595-23-0 ]

Esters

A237327 [89898-51-1]

Ethyl 4-oxotetrahydrofuran-3-carboxylate

Similarity: 0.97

A164864 [570-08-1]

Diethyl 2-acetylmalonate

Similarity: 0.86

A124799 [759-65-9]

Diethyl 2-methyl-3-oxosuccinate

Similarity: 0.84

A106668 [127956-11-0]

Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate

Similarity: 0.83

A176739 [517-23-7]

3-Acetyldihydrofuran-2(3H)-one

Similarity: 0.83

Ketones

A237327 [89898-51-1]

Ethyl 4-oxotetrahydrofuran-3-carboxylate

Similarity: 0.97

A164864 [570-08-1]

Diethyl 2-acetylmalonate

Similarity: 0.86

A124799 [759-65-9]

Diethyl 2-methyl-3-oxosuccinate

Similarity: 0.84

A106668 [127956-11-0]

Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate

Similarity: 0.83

A176739 [517-23-7]

3-Acetyldihydrofuran-2(3H)-one

Similarity: 0.83

Related Parent Nucleus of
[ 57595-23-0 ]

Tetrahydrofurans

A237327 [89898-51-1]

Ethyl 4-oxotetrahydrofuran-3-carboxylate

Similarity: 0.97

A176739 [517-23-7]

3-Acetyldihydrofuran-2(3H)-one

Similarity: 0.83

A118145 [19406-00-9]

Methyl 2-oxotetrahydrofuran-3-carboxylate

Similarity: 0.83

A163198 [77513-58-7]

Ethyl 2-oxotetrahydrofuran-3-carboxylate

Similarity: 0.83

A591889 [53662-85-4]

Methyl tetrahydrofuran-3-carboxylate

Similarity: 0.82

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