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[ CAS No. 3697-66-3 ] {[proInfo.proName]}

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Chemical Structure| 3697-66-3
Chemical Structure| 3697-66-3
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Product Details of [ 3697-66-3 ]

CAS No. :3697-66-3 MDL No. :MFCD08690114
Formula : C7H10O4 Boiling Point : -
Linear Structure Formula :- InChI Key :QQUZUWSSLUHHBP-UHFFFAOYSA-N
M.W : 158.15 Pubchem ID :11789472
Synonyms :

Calculated chemistry of [ 3697-66-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.71
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.45
TPSA : 63.6 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) : -6.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.46
Log Po/w (XLOGP3) : 0.52
Log Po/w (WLOGP) : 0.35
Log Po/w (MLOGP) : 0.21
Log Po/w (SILICOS-IT) : 0.68
Consensus Log Po/w : 0.64

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -0.88
Solubility : 20.7 mg/ml ; 0.131 mol/l
Class : Very soluble
Log S (Ali) : -1.43
Solubility : 5.92 mg/ml ; 0.0375 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.54
Solubility : 45.5 mg/ml ; 0.288 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.77

Safety of [ 3697-66-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3697-66-3 ]

* 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.

  • Upstream synthesis route of [ 3697-66-3 ]
  • Downstream synthetic route of [ 3697-66-3 ]

[ 3697-66-3 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 1559-02-0 ]
  • [ 3697-66-3 ]
YieldReaction ConditionsOperation in experiment
94%
Stage #1: With sodium hydroxide; water In ethanol for 16 h;
Stage #2: With hydrogenchloride In water
Synthesis of 1-(ethoxycarbonyl)cyclopropanecarboxylic acid Diethyl 1, 1-cyclopropane dicarboxylate (20g) was hydrolyzed in IN NaOH (107 m4) and ethanol (220D) for 16 hours, and the ethanol was removed by distillation under reduced pressure. The remaining starting material was removed by using ethyl acetate and the aqueous layer was acidified by IN HCI. The reaction mixture was extracted with ethyl acetate and distilled under reduced pressure. The residue was purified by silica gel column to give the title compound in a yield of 94percent. 1H NMR(CDCl3) No. 1.06 (t, 3H), 1.53 (m, 2H), 1.62 (m, 2H), 4.21 (q, 2H) ESI: 159 +1) +C7H1004
94%
Stage #1: With sodium hydroxide; water In ethanol for 16 h;
Stage #2: With hydrogenchloride In water
Synthesis of 1-(ethoxycarbonyl)cyclopropanecarboxylic acid Diethyl 1, 1-cyclopropane dicarboxylate (20g) was hydrolyzed in IN NaOH (107 m4) and ethanol (220D) for 16 hours, and the ethanol was removed by distillation under reduced pressure. The remaining starting material was removed by using ethyl acetate and the aqueous layer was acidified by IN HCI. The reaction mixture was extracted with ethyl acetate and distilled under reduced pressure. The residue was purified by silica gel column to give the title compound in a yield of 94percent. 1H NMR(CDCl3) No. 1.06 (t, 3H), 1.53 (m, 2H), 1.62 (m, 2H), 4.21 (q, 2H) ESI: 159 +1) +C7H1004
93% at 0 - 30℃; for 15 h; In the 2L three-mouth reaction bottle,Add 255.3 g of diethyl 1,1-cyclopropanedicarboxylate,840mL EtOH,The ice water bath cools it to 0 °C.Slowly add 137.32g KHCO3The temperature control is added below 30 °C.Naturally rise to room temperature,Stir the reaction for 15 h,TLC monitors the reaction completely,Add 1L of water,Extracted with (PE: EA = 1:1) 300 mL × 2,Remove the organic phase,Concentrated HCl adjusts pH=2,Extracted with EA 370mL×2,Take the organic phase,Desolvent1,1-cyclopropanedicarboxylic acid monoethyl ester 201.7 g,The yield was 93percent.
91%
Stage #1: With sodium hydroxide; water In ethanol at 20℃;
Stage #2: With hydrogenchloride In water
Step 1:
1,1-Cyclopropanedicarboxylic acid monoethyl ester
1 N NaOH (275 mL, 275 mmol) was added under nitrogen dropwise to a solution of 1,1-cyclopropanedicarboxylic acid diethyl ester (51.3121 g, 275 mmol) in 400 mL of absolute ethanol at room temperature.
After the addition, the reaction was allowed to stir at room temperature overnight.
The reaction was concentrated under reduced pressure to remove most of the ethanol.
The residue was partitioned between water and ether.
The aqueous layer was separated, extracted with ether, acidified with 2 N HCl and extracted four times with ether.
The combined extracts were dried (anhydrous MgSO4) and the solvent removed under reduced pressure to give a yellow oil.
The oil was dissolved in methylene chloride, dried (MgSO4), filtered and the solvent removed under reduced pressure to give 1,1-cyclopropanedicarboxylic acid monoethyl ester (39.8275 g, 91percent) as a yellow oil.
88.4% With potassium hydroxide In ethanol; water Step 2) 1-(Ethoxycarbonyl)cyclopropanecarboxylic acid
To a solution of diethyl cyclopropane-1,1-dicarboxylate (4.77 g, 25.6 mmol) in ethanol (40 mL) was added KOH (1.43 g, 25.6 mmol) in H2O (8 mL), and the reaction mixture was stirred at room temperature overnight.
The ethanol was removed under reduced pressure.
The residue was neutralized with HCl (6 mL, 5 mol/L), then extracted with EtOAc (100 mL*3).
The combined organic phases were dried over Na2SO4, filtered and the filtrate was concentrated in vacuo to give the title compound as a white solid (3.58 g, 88.4percent).
1H NMR (400 MHz, CDCl3): δ 1.27 (t, J=6.7 Hz, 3H), 1.83 (m, 2H), 1.86 (m, 2H), 4.25 (m, 2H).
88.4% at 20℃; To a solution of diethyl cyclopropane-1,1-dicarboxylate (4.77 g, 25.6 mmol) in ethanol (40 mL) was added KOH (1.43 g, 25.6 mmol) in H2O (8 mL), and the reaction mixture was stirred at room temperature overnight.
The ethanol was removed under reduced pressure.
The residue was neutralized with HCl (6 mL, 5 mol/L), then extracted with EtOAc (100 mL*3).
The combined organic phases were dried over Na2SO4, filtered and the filtrate was concentrated in vacuo to give the title compound as a white solid (3.58 g, 88.4 percent).
1H NMR (400MHz, CDCl3): δ 1.27 (t, J=6.7Hz, 3H), 1.83 (m, 2H), 1.86 (m, 2H), 4.25 (m, 2H).
88.4%
Stage #1: With water; potassium hydroxide In ethanol at 20℃; Inert atmosphere
Stage #2: With hydrogenchloride In ethanol; waterInert atmosphere
To a solution of diethyl cyclopropane- 1,1 -dicarboxylate (4.77 g, 25.6 mmol) in ethanol (40 mL) was added KOH (1.43 g, 25.6 mmol) in H2O (8 mL), and the reaction mixture was stirred at room temperature overnight. The ethanol was removed under reduced pressure. The residue was neutralized with HCl (6 mL, 5 mol/L), then extracted with EtOAc (100 mLx3). The combined organic phases were dried over Na2SO4, filtered and the filtrate was concentrated in vacuo to give the title compound as a white solid (3.58 g, 88.4 percent).1H NMR (400MHz, CDCl3): δ 1.27 (t, J=6.7Hz, 3H), 1.83 (m, 2H), 1.86 (m, 2H), 4.25 (m, 2H).
83% With potassium hydroxide In ethanol; water Monoethyl cyclopropane-1,1-dicarboxylate STR19
A solution of 53 g (285 mmol) of diethyl cyclopropane-1,1-dicarboxylate and 16.0 g (286 mmol) of potassium hydroxide in 300 ml of ethanol was stirred for 3 hours at 20° C. and then evaporated to dryness.
The residue was dissolved in 100 ml of water, after which byproducts were extracted with 200 ml of methylene chloride.
After the aqueous phase had been acidified to pH 2 with dilute hydrochloric acid, the product was extracted with 200 ml of methyl tert -butyl ether and isolated in a conventional manner.
Purification was carried out by distillation. Yield: 83percent; bp.: 99°-102° C. at 2.5 mbar; colorless oil.
79% With potassium hydroxide In ethanol at 20℃; KOH (2.8 g, 50 mmol), was added to a solution of IV-1 (9.3 g, 50 mmol) in 200 mL EtOH. The reaction mixture was stirred at rt overnight. After concentrated under reduced pressure, the residue was re-dissolved in 50 mL of NaHCO3 solution (w/w=5percent) and extracted with DCM. The aqueous layer was separated, and adjusted pH to 2 with 1N HCl, and extracted with EtOAc. The combined organic layer was dried and concentrated to afford IV-2 (6.0 g, yield 79percent), which was used to next step directly.
78.5% With sodium hydroxide In ethanol at 20℃; for 3 h; 500ml three-necked flask to 200ml of ethanol and 1,1-diethyl-cyclopropylamino burn 30g (161mmol), coldBut to l ° C, added dropwise with stirring a solution of sodium hydroxide (NaOH 6. 4g, 161mmol; water 32ml). Dropping was completed, the reaction at room temperature for 3 hours When the end of the reaction, the solvent was evaporated under reduced pressure to give a white solid. The solid was added water and ethyl acetate 200ml 100ml, stirring pointsLayer, the organic phase was discarded. Aqueous layer was washed with 2mol / L hydrochloric acid, adjusted to pH ρΗ3~4, ethyl acetate (100ml X 2) and extracted with ethyl acetateLayer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to give a colorless oil translucent 20. 0g (78. 5percent).
78.5% With sodium hydroxide In methanol; water at 20℃; for 3 h; To 500 ml of a three-necked flask was added 200 ml of methanol and 30 g of 1,1-cyclopropanedicarboxylic acid diethyl ester, cooled to 10 ° C, stir A solution of sodium hydroxide (NaOH 6.4 g, water 32 ml) was added dropwise, The reaction was carried out at room temperature for 3 hours, the reaction was terminated, the solvent was distilled off under reduced pressure, A white solid. To the solid was added 200 ml of water and 150 ml of ethyl acetate, ] Stir and layer, discard the organic phase. The aqueous layer was adjusted to pH 3 to 4 with 2 mol / L hydrochloric acid, Ethyl acetate extraction (200 ml x 2), The organic phase was dried over anhydrous sodium sulfate, filtered, The solvent was distilled off under reduced pressure, To give a colorless translucent oil
64.6% With sodium hydroxide In tetrahydrofuran; methanol at 25℃; for 16 h; Inert atmosphere Ethyl 1,1-cyclopropyl dicarbonate (1.0 g, 5.37 mmol) was added to tetrahydrofuran (3 ml) at 25 °C under the protection of nitrogen, then a mixed solution of sodium hydroxide/methanol (1 mol/L, 5.37 ml) was added thereto, and the mixture was stirred under the protection of nitrogen for 16 hours at 25 °C. The solution was concentrated under reduced pressure at 30 °C and then added to water (20 ml). The aqueous phase was washed with ethyl acetate (20 ml * 2), the pH was adjusted to 2 with hydrochloric acid (2 mol/L) (20 ml * twice) and extracted with ethyl acetate (20 ml * 2). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated to give compound 168A (creamy white solid, 500 mg, the yield was 64.6percent). 1H NMR (400 MHz, CHLOROFORM-d) 3.79 (s, 3H), 1.80-1.88 (m, 2H), 1.72-1.79 (m, 2H)
6 g at 25℃; for 12 h; A solution of 1,1-diethyl cyclopropane-1,1-dicarboxylate (10.00 g, 53.70 mmol, 1.00 equiv), sodium hydroxide (2.15 g, 53.75 mmol, 1.00 equiv) in ethanol (50 mL) was stirred for 12 h at 25 oC. After completion, the solids were collected by filtration and re-crystallized from ethanol. This resulted in 6 g of the title compound as a white solid.

Reference: [1] Patent: WO2005/79812, 2005, A1, . Location in patent: Page/Page column 45-46
[2] Patent: WO2005/79812, 2005, A1, . Location in patent: Page/Page column 45-46
[3] Patent: CN105111155, 2018, B, . Location in patent: Paragraph 0038; 0051; 0055; 0056
[4] Patent: US2008/45556, 2008, A1, . Location in patent: Page/Page column 21
[5] Patent: US2010/239576, 2010, A1,
[6] Patent: EP2408300, 2016, B1, . Location in patent: Paragraph 0384
[7] Patent: WO2010/45095, 2010, A1, . Location in patent: Page/Page column 99
[8] Synthetic Communications, 1988, vol. 18, # 2, p. 141 - 150
[9] Patent: US5371268, 1994, A,
[10] Journal of Medicinal Chemistry, 2009, vol. 52, # 21, p. 6790 - 6802
[11] Patent: US2014/200215, 2014, A1, . Location in patent: Paragraph 0961; 0962
[12] Patent: CN103664776, 2016, B, . Location in patent: Paragraph 0066; 0067; 0068
[13] Patent: CN103965104, 2017, B, . Location in patent: Paragraph 0124-0126
[14] Journal of Medicinal Chemistry, 1988, vol. 31, # 10, p. 2004 - 2008
[15] Journal of Fluorine Chemistry, 2000, vol. 104, # 2, p. 297 - 301
[16] Tetrahedron, 2010, vol. 66, # 51, p. 9733 - 9737
[17] Patent: EP3293177, 2018, A1, . Location in patent: Paragraph 0380; 0381
[18] Synthetic Communications, 1996, vol. 26, # 11, p. 2127 - 2133
[19] Patent: US4766145, 1988, A,
[20] Patent: EP2471792, 2012, A1, . Location in patent: Page/Page column 66
[21] Chemistry - A European Journal, 2012, vol. 18, # 51, p. 16531 - 16539
[22] Patent: WO2013/91502, 2013, A1, . Location in patent: Page/Page column 43
[23] Patent: US2014/329800, 2014, A1, . Location in patent: Paragraph 0124; 0370
[24] Molecules, 2016, vol. 21, # 5,
[25] Patent: CN105218445, 2016, A, . Location in patent: Paragraph 0044-0046
[26] Journal of Medicinal Chemistry, 2017, vol. 60, # 21, p. 9067 - 9089
[27] Patent: WO2018/83105, 2018, A1, . Location in patent: Page/Page column 192
  • 2
  • [ 64-17-5 ]
  • [ 34867-88-4 ]
  • [ 3697-66-3 ]
Reference: [1] Mendeleev Communications, 2016, vol. 26, # 1, p. 14 - 15
  • 3
  • [ 105-53-3 ]
  • [ 3697-66-3 ]
Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 51, p. 16531 - 16539
[2] Molecules, 2016, vol. 21, # 5,
[3] Patent: EP2408300, 2016, B1,
[4] Patent: CN105111155, 2018, B,
  • 4
  • [ 3697-66-3 ]
  • [ 3697-68-5 ]
YieldReaction ConditionsOperation in experiment
61%
Stage #1: With triethylamine; isobutyl chloroformate In tetrahydrofuran at -10 - 0℃; for 1 h;
Stage #2: With sodium tetrahydroborate; water In tetrahydrofuran at 0℃; for 1 h;
To a stirring solution of compound 71 (1 .0 g, 6.32 mmol) and triethylamine (0.97 ml, 7.59 mmol) in THF (18 ml) at -10 °C, was added isobutyl chloroformate (0.90 ml, 6.96 mmol) dropwise. Then the reaction mixture was stirred 1 h at 0°C, the insoluble material was filtered off, and the filtrate was directly used later. To an ice-cooling solution of NaBH4 (0.71 g, 18.97 mmol) in THF (10 ml) and water (2.5 ml), was added the filtrate obtained above dropwise. After the reaction mixture was allowed to stirred at 0°C for 1 h, then reaction mixture was poured into 10percent of aqueous solution HOAc, the aqueous phase was extracted with EtOAc (30 ml x 3), and the combined organic phase was washed with brine, dried over Na2S04, filtered and concentrated to afford crude product, which was purified by silica gel column chromatography (Petroleum ether: ethyl acetate = 9: 1 to 2:1 ) to give compound 72 (0.65 g, yield 61 percent) as a colorless oil. HNMR (CDCI3): δ 4.15(2H, q, J=7.0Hz), 3.62(2H, s), 1.28-1.23(5H, m), 0.86(2H, q, J=4.2Hz)
Reference: [1] Patent: WO2013/91502, 2013, A1, . Location in patent: Page/Page column 43
[2] Tetrahedron, 2010, vol. 66, # 51, p. 9733 - 9737
  • 5
  • [ 3697-66-3 ]
  • [ 108-23-6 ]
  • [ 3697-68-5 ]
YieldReaction ConditionsOperation in experiment
0.65 g
Stage #1: With triethylamine In tetrahydrofuran at -10 - 0℃; for 1 h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 0℃; for 1 h;
[0371] To a stirring solution of compound 71 (1.0 g, 6.32mmol) and triethylamine (0.97 ml, 7.59 mmol) in THF (18ml) at -10° C., was added isobutyl chloroformate (0.90 ml,6.96 mmol) dropwise. Then the reaction mixture was stirred1 h at oo C., the insoluble material was filtered off, and thefiltrate was directly used later. To an ice-cooling solution ofNaBH4 (0.71 g, 18.97 mmol) in THF (10 ml) and water (2.5ml), was added the filtrate obtained above dropwise. After thereaction mixture was allowed to stirred at oo C. for 1 h, thenreaction mixture was poured into 10percent of aqueous solutionHOAc, the aqueous phase was extracted with EtOAc (30mlx3), and the combined organic phase was washed withbrine, dried over Na2S04 , filtered and concentrated to affordcrude product, which was purified by silica gel column chromatography(Petroleum ether: ethyl acetate=9: 1 to 2:1) to givecompound 72 (0.65 g, yield 61 percent) as a colorless oil.[0372] 1HNMR (CDCI3): ll 4.15 (2H, q, 1=7.0 Hz), 3.62(2H, s), 1.28-1.23 (5H, m), 0.86 (2H, q, 1=4.2 Hz)
Reference: [1] Patent: US2014/329800, 2014, A1, . Location in patent: Paragraph 0124; 0371 0372
  • 6
  • [ 3697-66-3 ]
  • [ 42303-42-4 ]
Reference: [1] Patent: US2008/45556, 2008, A1,
  • 7
  • [ 3697-66-3 ]
  • [ 89544-83-2 ]
Reference: [1] Synthesis, 1983, # 11, p. 915 - 916
  • 8
  • [ 3697-66-3 ]
  • [ 75-65-0 ]
  • [ 107259-05-2 ]
YieldReaction ConditionsOperation in experiment
91% at 20℃; for 5 h; Heating / reflux Step 2:
1-[[(1,1-Dimethylethoxy)carbonyl]amino]cyclopropane carboxylic acid ethyl ester
Triethylamine (29.82 mL, 214 mmol) was added under nitrogen dropwise to a mixture of 1,1-cyclopropanedicarboxylic acid monoethyl ester (31.518 g, 199 mmol), prepared in the previous step, and diphenylphosphoryl azide (47.4 mL, 219 mmol) in 40 mL of tert-butanol at room temperature.
After the addition, the reaction was refluxed for 5 h.
The reaction was concentrated under reduced pressure.
The residue was taken up in ethyl acetate and extracted three times each with 5percent citric acid, saturated NaHCO3 and saturated NaCl.
The ethyl acetate layer was dried (anhydrous MgSO4), filtered and the solvent removed under reduced pressure to give 1-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopropane carboxylic acid ethyl ester (41.3931 g, 91percent) as a yellow oil, MS (ES) m/z 130.0 [M+H-tBoc].
Reference: [1] Patent: US2008/45556, 2008, A1, . Location in patent: Page/Page column 21
[2] Journal of Medicinal Chemistry, 1988, vol. 31, # 10, p. 2004 - 2008
[3] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 7, p. 1442 - 1454
  • 9
  • [ 3697-66-3 ]
  • [ 7440-47-3 ]
  • [ 7440-02-0 ]
  • [ 7439-98-7 ]
  • [ 139229-57-5 ]
YieldReaction ConditionsOperation in experiment
76% With hydrogen fluoride In dichloromethane Ethyl 1-trifluoromethylcyclopropanecarboxylate STR20
31.6 g (0.20 mol) of monoethyl cyclopropane-1,1-dicarboxylate, 126 g (1.16 mol) of sulfur tetrafluoride, 100 ml of dichloromethane and 1.5 g (75 mmol) of hydrogen fluoride were introduced at -70° C. into a 500 ml stirred autoclave which was lined with an alloy of 70percent of nickel, 15percent of chromium and 15percent of molybdenum.
The mixture was heated for 48 hours at 80° C. and the gaseous constituents were destroyed, after cooling the autoclave to 35° C., by passing them into a wash tower filled with potassium hydroxide.
The residue was dissolved in 100 ml of dichloromethane.
The solution was washed with 100 ml of saturated sodium bicarbonate solution, after which the organic phase was dried with sodium sulfate and potassium fluoride and was separated into the individual components by distillation. Yield: 76percent; bp.: 141°-142° C.; oil.
Reference: [1] Patent: US5371268, 1994, A,
  • 10
  • [ 3697-66-3 ]
  • [ 139229-57-5 ]
Reference: [1] Journal of Fluorine Chemistry, 2000, vol. 104, # 2, p. 297 - 301
  • 11
  • [ 3697-66-3 ]
  • [ 849217-48-7 ]
Reference: [1] Patent: EP2408300, 2016, B1,
[2] Patent: CN105218445, 2016, A,
  • 12
  • [ 3697-66-3 ]
  • [ 849217-64-7 ]
Reference: [1] Patent: CN105218445, 2016, A,
[2] Patent: CN103965104, 2017, B,
[3] Patent: CN103965104, 2017, B,
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