* 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.
As previously described,7 chlorosulfonyl isocyanate (1.0 mL, 11 mmol) was reacted with vinyl acetate (5.0 mL, 54 mmol) in dry CH2Cl2 for 2 h at 0 oC, leading to the generation of the title compound (9, 0.50 g, 35percent). The spectral data of 9 were in good agreement with the reported results.7
127.8 g
Stage #1: at 3℃; for 48 h; Inert atmosphere
In a four-necked flask with a volume of 1 L, which was equipped with a dropping funnel, a thermometer, and a nitrogen introducing tube, 189.4 g (2.2 mol) of vinyl acetate was charged, and 56.6 g (0.4 mol) of chlorosulfonyl isocyanate was added dropwise at 3° C. After completion of the dropwise addition, the mixture was further stirred at 3° C. for 48 hours. The obtained reaction mixture was added dropwise to 174 g of sodium sulfite, 93 g of sodium hydrogencarbonate, and 1,500 g of water and hydrolyzed. The resultant was extracted three times with 500 g of chloroform. The organic layer was concentrated under reduced pressure, thereby obtaining 127.8 g (1.0 mol) of 3-acetoxyazetidinone having the following properties. 1H-NMR (400 MHz, CDCl3, ppm, TMS) δ: 2.11 (3H, s), 2.99 (1H, dd, J=15.4, 1.2 Hz), 3.27 (1H, dd, J=15.4, 4.0 Hz), 5.84 (1H, dd, J=4.0, 1.2 Hz), 7.20 (1H, br)
Reference：
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 17, p. 2055 - 2068
[2] Bulletin of the Korean Chemical Society, 2014, vol. 35, # 10, p. 2990 - 2994
[3] Journal of Organic Chemistry, 2008, vol. 73, # 13, p. 5015 - 5021
[4] Synthesis, 1987, # 3, p. 324
[5] Patent: US8859183, 2014, B2, . Location in patent: Paragraph 0258-0261
With peracetic acid; sodium acetate; acetic acid In acetonitrile
EXAMPLE 2 Synthesis of 4-acetoxyazetidine-2-one 0.71 g of azetidine-2-one and 0.82 g of anhydrous sodium acetate were suspended in 20 ml of acetonitrile and cooled to -5°, to which 10 ml of acetonitrile containing 0.26 g of ruthenium trichloride.3H2 O was added. 3.8 ml of acetic acid containing 40percent peracetic acid was carefully dropped thereto so as to maintain the temperature not higher than 0° C., then continuously stirred at 0° C. for 30 minutes. The solvent was distilled off under reduced pressure at a temperature not higher than 40° C., and subjected to silica gel chromatography (eluent: n-hexane: ethyl acetate=1:1) for purification to obtain 0.92 g of the title compound (yield 71percent). 1 H-NMR(CDCl3) δ ppm: 2.13(3H, s), 3.00(1H, ddd, J=15.26 Hz, 1.40 Hz, 0.45 Hz), 3.26(1H, ddd, J=15.26, 4.05, 2.58), 5.84(1H, dd, J=4.05 Hz, 1.40 Hz), 7.02(1H, bs, --NH)
71%
With peracetic acid; sodium acetate; acetic acid In acetonitrile
EXAMPLE 2 Synthesis of 4-acetoxyazetidine-2-one 0.71 g of azetidine-2-one and 0.82 g of anhydrous sodium acetate were suspended in 20 ml of acetonitrile and cooled to -5° C., to which 10 ml of acetonitrile containing 0.26 g of ruthenium trichloride.3H2 O was added. 3.8 ml of acetic acid containing 40percent peracetic acid was carefully dropped thereto so as to maintain the temperature not higher than 0° C., then continuously stirred at 0° C. for 30 minutes. The solvent was distilled off under reduced pressure at a temperature not higher than 40° C., and subjected to silica gel chromatography (eluent: n-hexane:ethyl acetate=1:1) for purification to obtain 0.92 g of the title compound (yield 71percent). 1 H NMR(CDCl3)δppm: 2.13(3H, s), 3.00(1H, ddd, J=15.26, 1.40, 0.45), 3.26(1H, ddd, J=15.26, 4.05, 2.58), 5.84(1H, dd, J=4.05, 1.40), 7.02(1H, bs, --NH).
Reference：
[1] Patent: US5204460, 1993, A,
[2] Patent: US5081239, 1992, A,
4
[ 930-21-2 ]
[ 28562-53-0 ]
Yield
Reaction Conditions
Operation in experiment
78%
With peracetic acid; sodium acetate; acetic acid In water; ethyl acetate
EXAMPLE 1 Synthesis of 4-Acetoxyazetidin-2-one To a mixture of 200 mg (2.8 mmole) of azetidin-2-one, 230 mg (2.8 mmole) of anhydrous sodium acetate, 2 ml of acetic acid, and 17 mg (2 mole percent based on the amount of azetidin-2-one) of osmium trichloride trihydrate was added dropwise, with stirring, 1.56 g (6.2 mmole) of a 30percent peracetic acid solution in ethyl acetate at room temperature over a period of 2 hours or more. The reaction mixture was poured into 50 ml of water and extracted with n-hexane. The extract was separated and purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1 by volume). Thus, 280 mg (2.2 mmole, percent yield: 78percent) of 4-acetoxyazetidin-2-one in a colorless oily state was obtained.
With sodium hydrogencarbonate; sodium sulfite In dichloromethane; water at 0℃; for 0.5 h;
To a stirred solution of vinyl acetate (4, 5.0 mL, 54 mmol) in dry CH2Cl2 (5 mL) was added chlorosulfonyl isocyanate (5, 1.0 mL, 11 mmol) dropwise at 0 °C. After stirring for 2 h at 0 °C, the mixture was poured into an aqueous solution (150 mL) of NaHCO3 (8 g) and Na2SO3 (8 g) at 0 oC with stirring. Stirring was again continued for 30 min at 0 °C and the mixture was extracted with CH2Cl2. Evaporation of the solvent gave a yellow oil that was chromatographed on silica gel to afford the title compound (0.50 g, 35percent).#10;
Reference：
[1] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 1, p. 121 - 127
[2] Organic Syntheses, 1987, vol. 65, p. 135 - 135
7
[ 930-21-2 ]
[ 79-21-0 ]
[ 28562-53-0 ]
Reference：
[1] Journal of the American Chemical Society, 1990, vol. 112, # 21, p. 7820 - 7822
8
[ 79-21-0 ]
[ 98019-65-9 ]
[ 28562-53-0 ]
Reference：
[1] Journal of the American Chemical Society, 1990, vol. 112, # 21, p. 7820 - 7822
9
[ 930-21-2 ]
[ 28562-53-0 ]
Reference：
[1] Patent: US5204460, 1993, A,
10
[ 127756-72-3 ]
[ 28562-53-0 ]
Reference：
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 2, p. 277 - 282
11
[ 80395-83-1 ]
[ 64-19-7 ]
[ 28562-53-0 ]
Reference：
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 11, p. 1283 - 1284
With sodium hydrogencarbonate In water; acetone at 20℃; for 12h; Inert atmosphere;
11 5.1.1. General procedure for synthesis of β-lactams containing aromatic thiols, phenol and benzeneselenol
General procedure: Synthesis of compounds 2-28 was performed using procedures adapted from Grimm and co-workers20 and Wasserman et al.21 To a solution of 4-acetoxy-2-azetidinone 1 (1 g; 8 mmol in 50 ml acetone/water, 3:2) 1.05 mol equiv of thiophenols, phenol or benzeneselenol, respectively, were added. Sodium bicarbonate (4 mol equiv) was added and the mixture was stirred vigorously (12 h; closed round bottom flask). Sodium chloride was added to the solution until two layers were formed. The mixture was then filtered and extracted (EtOAc; 3×50 ml). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude product was purified by a variety of methods (preparative HPLC; flash chromatography; and/or recrystallization). 5.1.1.11 4-(4-Nitro-phenylsulfanyl)-azetidin-2-one (12) The product was purified by recrystallization in ethyl acetate/hexanes to give white crystals (81%) with mp 124.03 °C. 1H NMR (400 MHz, CDCl3): δ 8.20 (2H, dd, J = 2.0, 8.4), 7.48 (2H, dd, J = 3.1, 8.5), 6.24 (1H, br s), 5.22 (1H, dd, J = 2.3, 4.9), 3.58 (1H, ddd, J = 1.7, 8.7, 15.7), 3.05 (1H, ddd, J = 1.5, 7.9, 15.7); 13C NMR (100 MHz, CDCl3) δ 165.95, 130.93, 128.60, 119.92, 119.70, 115.88, 115.67, 54.21, 45.81; IR (neat) νmax (C=O) 1700 cm-1. Anal. Calcd for C9H8N2O3S: C, 48.21; H, 3.60; N, 12.49. Found: C, 48.16; H, 3.50; N, 12.39.
With potassium hydroxide In methanol; water at 0 - 10℃; for 0.5h;
4-(3,4-dimethoxy-phenylsulfanyl)-azetidin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
63%
With sodium hydrogencarbonate; In water; acetone; at 20℃; for 12h;Inert atmosphere;
General procedure: Synthesis of compounds 2-28 was performed using procedures adapted from Grimm and co-workers20 and Wasserman et al.21 To a solution of 4-acetoxy-2-azetidinone 1 (1 g; 8 mmol in 50 ml acetone/water, 3:2) 1.05 mol equiv of thiophenols, phenol or benzeneselenol, respectively, were added. Sodium bicarbonate (4 mol equiv) was added and the mixture was stirred vigorously (12 h; closed round bottom flask). Sodium chloride was added to the solution until two layers were formed. The mixture was then filtered and extracted (EtOAc; 3×50 ml). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude product was purified by a variety of methods (preparative HPLC; flash chromatography; and/or recrystallization). 5.1.1.20 4-(3,4-Dimethoxy-phenylsulfanyl)-azetidin-2-one (21) The product was purified by recrystallization in hexanes/ethyl acetate to give a white powder (63%) with mp 79-80 C. 1H NMR (400 MHz, CDCl3): δ 7.07-6.34 (4H, m), 6.36 (1H, br s), 4.71 (1H, dd, J = 2.3, 4.9), 3.68 (3H, s), 3.67 (3H, s), 3.10 (1H, ddd, J = 1.9, 8.4, 15.7), 2.64 (1H, ddd, J = 1.6, 8.3, 15.7); 13C NMR (100 MHz, CDCl3) δ 171.20, 166.21, 150.12, 149.15, 128.05, 121.20, 117.74, 111.59, 60.41, 56.02, 55.91, 54.78, 44.89, 21.06, 14.19; IR (neat) νmax (C=O) 1760 cm-1. Anal. Calcd for C11H13NO3S: C, 55.21; H, 5.48; N, 5.85. Found: C, 55.03; H, 5.40; N, 5.78.
With nitrogen; sodium; In ethanol; water;
a. 4-(3,4-Dimethoxyphenylthio)azetidin-2-one Sodium (0.9 g, 39 mmol) was dissolved in ethanol (150 ml) and <strong>[700-96-9]3,4-dimethoxythiophenol</strong> (5.9 g, 35 mmol) added dropwise over 20 minutes keeping the temperature between 20 C.-25 C. whilst bubbling nitrogen through the mixture. After 15 minutes, the reaction was cooled to 5 C. and a solution of 4-acetoxyazetidin-2-one (4.3 g, 33 mmol) in ethanol (50 ml) was added dropwise over 15 minutes whilst maintaining the temperature at 5 C. The mixture was stirred at room temperature for 60 minutes and evaporated to dryness under reduced pressure. Water (400 ml) was added, the mixture extracted with dichloromethane (2*300 ml), the extracts dried (MgSO4) and evaporated under reduced pressure to an oil. The oil was cooled to -20 C. and titurated with ether (400 ml) to give a white solid which was isolated by filtration (4.1 g, 52%) m.p. 145-6 C. 1 H NMR δ (CDCl3) 2.85 (1H, m, H3a), 3.31 (1H, m, H3b), 3.88 (3H, s, O--CH3), 3.89 (3H, s, O--CH3), 4.92 (1H, dd, J=4.92, 2.30 Hz, H4), 6.30 (1H, br. singlet, N--H), 6.85 (1H, d, J=8.30 Hz, Ph--H), 7.00 (1H, d, J=2.04 Hz, Ph--H), 7.09 (1H, dd, J=8.25, 2.06 Hz, Ph--H).
With sodium hydrogencarbonate; In water; acetone; at 20℃; for 12h;
General procedure: Lactams 22 and 24, as well as 26-28 were prepared in a manner similar to the synthesis of lactam 9. 4-Acetoxy-2-azetidone (1 g, 8 mmol) was stirred in 50 mL acetone/water (3:2) and 1.05 equiv of the corresponding substituents (4-mercaptophenol, 4-aminothiophenol, 1,4-benzenedithiol, thiophenol, or 2-thiophene thiol, respectively) was added. Sodium bicarbonate (4 equiv) was added to the mixture, which was then stirred vigorously for 12 h in a closed round bottom flask. Sodium chloride was subsequently added to the solution and after the formation of two layers, the mixture was filtered out and extracted with AcOEt (3 × 50 mL). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude material was purified by flash chromatography or crystallized to give white crystals for all five products in good yield (30-66%).
90%
With sodium hydrogencarbonate; In water; acetone; at 20℃; for 12h;Inert atmosphere;
Synthesis of compounds 2-28 was performed using procedures adapted from Grimm and co-workers20 and Wasserman et al.21 To a solution of 4-acetoxy-2-azetidinone 1 (1 g; 8 mmol in 50 ml acetone/water, 3:2) 1.05 mol equiv of thiophenols, phenol or benzeneselenol, respectively, were added. Sodium bicarbonate (4 mol equiv) was added and the mixture was stirred vigorously (12 h; closed round bottom flask). Sodium chloride was added to the solution until two layers were formed. The mixture was then filtered and extracted (EtOAc; 3×50 ml). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude product was purified by a variety of methods (preparative HPLC; flash chromatography; and/or recrystallization). 5.1.1.21 4-(Thiophen-2-ylsulfanyl)-azetidin-2-one (22) The crude product was crystallized from hexanes/methylene chloride to afford white crystals (90%) with mp 57-58 C. 1H NMR (400 MHz,CDCl3): delta 7.48 (1H, dd, J = 1.2, 5.4), 7.23 (1H, dd, J = 1.2, 3.6), 7.07 (1H, dd, J = 3.6, 5.4), 6.19 (1H, br s), 4.86 (1H, dd, J = 2.3, 4.9), 3.31 (1H, ddd, J = 1.9, 4.9, 15.3), 2.91 (1H, ddd, J = 1.6, 2.0, 15.2); 13C NMR (100 MHz, CDCl3) delta 165.52, 136.75, 131.82, 128.12, 127.49, 55.38, 44.72; IR (neat) numax (C=O) 1739.7.1 cm-1. Anal. Calcd for C7H7NOS2: C, 45.38; H, 3.81; N, 7.56. Found: C, 45.50; H, 3.76; N, 7.43.
With sodium hydrogencarbonate In water; acetone at 20℃; for 12h;
4.3.17. General procedure for synthesis of β-lactams containing aromatic thiols, phenol and thiophene
General procedure: Lactams 22 and 24, as well as 26-28 were prepared in a manner similar to the synthesis of lactam 9. 4-Acetoxy-2-azetidone (1 g, 8 mmol) was stirred in 50 mL acetone/water (3:2) and 1.05 equiv of the corresponding substituents (4-mercaptophenol, 4-aminothiophenol, 1,4-benzenedithiol, thiophenol, or 2-thiophene thiol, respectively) was added. Sodium bicarbonate (4 equiv) was added to the mixture, which was then stirred vigorously for 12 h in a closed round bottom flask. Sodium chloride was subsequently added to the solution and after the formation of two layers, the mixture was filtered out and extracted with AcOEt (3 × 50 mL). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude material was purified by flash chromatography or crystallized to give white crystals for all five products in good yield (30-66%).
4-(2-fluoro-phenylsulfanyl)-azetidin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
65%
With sodium hydrogencarbonate In water; acetone at 20℃; for 12h; Inert atmosphere;
2 5.1.1. General procedure for synthesis of β-lactams containing aromatic thiols, phenol and benzeneselenol
General procedure: Synthesis of compounds 2-28 was performed using procedures adapted from Grimm and co-workers20 and Wasserman et al.21 To a solution of 4-acetoxy-2-azetidinone 1 (1 g; 8 mmol in 50 ml acetone/water, 3:2) 1.05 mol equiv of thiophenols, phenol or benzeneselenol, respectively, were added. Sodium bicarbonate (4 mol equiv) was added and the mixture was stirred vigorously (12 h; closed round bottom flask). Sodium chloride was added to the solution until two layers were formed. The mixture was then filtered and extracted (EtOAc; 3×50 ml). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude product was purified by a variety of methods (preparative HPLC; flash chromatography; and/or recrystallization). 5.1.1.2 4-(2-Fluoro-phenylsulfanyl)-azetidin-2-one (3) The product was purified by flash chromatography from ethyl acetate/hexanes to give white crystals (65%) yield with mp 101.83 °C. 1H NMR (400 MHz, CDCl3): δ 7.30 (5H, m), 6.16 (1H, br s), 4.99 (1H, dd, J = 2.3, 5.0), 3.36 (1H, ddd, J = 2.4, 7.8, 15.7), 2.87 (1H, dd, J = 1.3, 7.8, 15.7). 13C NMR (100 MHz, CDCl3) δ 165.75, 164.02, 161.57, 136.30, 131.40, 125.06, 116.62, 114.89, 54.44, 46.04; IR (neat) νmax (C=O) 1750 cm-1; X-ray analyses.fx2
4-(3-4luoro-phenylsulfanyl)-azetidin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
65%
With sodium hydrogencarbonate In water; acetone at 20℃; for 12h; Inert atmosphere;
3 5.1.1. General procedure for synthesis of β-lactams containing aromatic thiols, phenol and benzeneselenol
General procedure: Synthesis of compounds 2-28 was performed using procedures adapted from Grimm and co-workers20 and Wasserman et al.21 To a solution of 4-acetoxy-2-azetidinone 1 (1 g; 8 mmol in 50 ml acetone/water, 3:2) 1.05 mol equiv of thiophenols, phenol or benzeneselenol, respectively, were added. Sodium bicarbonate (4 mol equiv) was added and the mixture was stirred vigorously (12 h; closed round bottom flask). Sodium chloride was added to the solution until two layers were formed. The mixture was then filtered and extracted (EtOAc; 3×50 ml). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude product was purified by a variety of methods (preparative HPLC; flash chromatography; and/or recrystallization). 5.1.1.3 4-(3-Fluoro-phenylsulfanyl)-azetidin-2-one (4) The product was purified by flash chromatography from ethyl acetate/hexanes to give white crystals (65%) with mp 60.94 °C. 1H NMR (400 MHz, CDCl3): δ 7.30 (5H, m), 6.16 (1H, br s), 4.99 (1H, dd, J = 2.3, 4.9), 3.36 (1H, ddd, J = 1.8, 7.8, 15.7), 2.87 (1H, dd, J = 1.3, 7.8, 15.7); 13C NMR (100 MHz, CDCl3) δ 165.95, 160.92, 130.93, 128.60, 119.92, 119.70, 115.67, 54.21, 45.81; IR (neat) νmax (C=O) 1750 cm-1. Anal. Calcd for C17H14F2N2O2S: C, 58.61; H, 4.05; N, 8.04. Found: C, 58.29; H, 3.99; N, 8.07.
4-(2,4-difluoro-phenylsulfanyl)-azetidin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
70%
With sodium hydrogencarbonate; In water; acetone; at 20℃; for 12h;Inert atmosphere;
General procedure: Synthesis of compounds 2-28 was performed using procedures adapted from Grimm and co-workers20 and Wasserman et al.21 To a solution of 4-acetoxy-2-azetidinone 1 (1 g; 8 mmol in 50 ml acetone/water, 3:2) 1.05 mol equiv of thiophenols, phenol or benzeneselenol, respectively, were added. Sodium bicarbonate (4 mol equiv) was added and the mixture was stirred vigorously (12 h; closed round bottom flask). Sodium chloride was added to the solution until two layers were formed. The mixture was then filtered and extracted (EtOAc; 3×50 ml). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude product was purified by a variety of methods (preparative HPLC; flash chromatography; and/or recrystallization). 5.1.1.5 4-(2,4-Difluoro-phenylsulfanyl)-azetidin-2-one (6) The product was purified by recrystallization in ethyl acetate/hexanes to give white crystals (70%) with mp 70-73 C. 1H NMR (400 MHz, CDCl3): delta 7.52 (1H, dd, J = 0.5, 8.8), 6.85 (1H, ddd, J = 2.7, 5.1, 8.8), 6.78 (1H, ddd, J = 0.5, 2.7, 5.1), 6.13 (1H, br s), 4.96 (1H, dd, J = 2.3, 4.9), 3.42 (1H, ddd, J = 1.8, 8.5, 15.7), 2.29 (1H, ddd, J = 1.8, 7.8, 15.6); 13C NMR (100 MHz, CDCl3) delta 166.43, 165.01, 161.90, 139.36, 112.31, 11.34, 104.88, 54.38, 45.55; IR (neat) numax (C=O) 1750 cm-1. Anal. Calcd for C9H7F2NOS: C, 50.23; H, 3.28; N, 6.51. Found: C, 50.32; H, 3.30; N, 6.35.
4-(3,4-difluoro-phenylsulfanyl)-azetidin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
47.1%
With sodium hydrogencarbonate In water; acetone at 20℃; for 12h; Inert atmosphere;
6 5.1.1. General procedure for synthesis of β-lactams containing aromatic thiols, phenol and benzeneselenol
General procedure: Synthesis of compounds 2-28 was performed using procedures adapted from Grimm and co-workers20 and Wasserman et al.21 To a solution of 4-acetoxy-2-azetidinone 1 (1 g; 8 mmol in 50 ml acetone/water, 3:2) 1.05 mol equiv of thiophenols, phenol or benzeneselenol, respectively, were added. Sodium bicarbonate (4 mol equiv) was added and the mixture was stirred vigorously (12 h; closed round bottom flask). Sodium chloride was added to the solution until two layers were formed. The mixture was then filtered and extracted (EtOAc; 3×50 ml). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude product was purified by a variety of methods (preparative HPLC; flash chromatography; and/or recrystallization). 5.1.1.6 4-(3,4-Difluoro-phenylsulfanyl)-azetidin-2-one (7) The product was purified by recrystallization in ethyl acetate/hexanes to give white crystals (47.1%) with mp 74-77 °C. 1H NMR (400 MHz, CDCl3): δ 7.11-7.37 (3H, m), 6.17 (1H, br s), 5.00 (1H, dd, J = 2.3, 4.9), 3.64 (1H, ddd, J = 1.7, 7.8, 15.7), 2.90 (1H, ddd, J = 1.6, 7.8, 15.7); 13C NMR (100 MHz, CDCl3) δ 166.53, 151.87, 149.89, 130.77, 127.39, 123.23, 118.33, 54.70, 45.45; IR (neat) νmax (C=O) 1750 cm-1. Anal. Calcd for C9H7F2NOS: C, 50.23; H, 3.28; N, 6.51. Found: C, 50.15; H, 3.26; N, 6.45.
With sodium hydrogencarbonate In water; acetone at 20℃; for 12h; Inert atmosphere;
8 5.1.1. General procedure for synthesis of β-lactams containing aromatic thiols, phenol and benzeneselenol
General procedure: Synthesis of compounds 2-28 was performed using procedures adapted from Grimm and co-workers20 and Wasserman et al.21 To a solution of 4-acetoxy-2-azetidinone 1 (1 g; 8 mmol in 50 ml acetone/water, 3:2) 1.05 mol equiv of thiophenols, phenol or benzeneselenol, respectively, were added. Sodium bicarbonate (4 mol equiv) was added and the mixture was stirred vigorously (12 h; closed round bottom flask). Sodium chloride was added to the solution until two layers were formed. The mixture was then filtered and extracted (EtOAc; 3×50 ml). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude product was purified by a variety of methods (preparative HPLC; flash chromatography; and/or recrystallization). 5.1.1.8 4-(2-Chloro-4-fluoro-phenylsulfanyl)-azetidin-2-one (9) The product was purified by recrystallization in ethyl acetate/hexanes to give white crystals (66%) mp 84-85 °C. 1H NMR (400 MHz, CDCl3): δ 7.56 (1H, dd, J = 0.5, 8.8), 7.20 (ddd, J = 0.5, 2.6, 5.5), 7.04 (1H, ddd, J = 2.6, 5.5, 8.8), 6.46 (1H, br s), 5.02 (1H, dd, J = 2.4, 4.8), 3.45 (1H, ddd, J = 1.8, 3.0, 8.5), 2.97 (1H, td, J = 1.8, 11.6); 13C NMR (100 MHz, CDCl3): δ 165.65, 164.32, 161.78, 137.58, 126.45, 118.63, 115.09, 54.36, 45.81; IR (neat) νmax (C=O) 1756.93 cm-1. Anal. Calcd for C9H7ClFNOS: C, 46.66; H, 3.05; Cl, 15.30; F, 8.20; N, 6.05; O, 6.91; S, 13.84. Found: C, 46.97; H, 3.23; Cl, 15.51; F, 8.13; N, 6.22; O, 6.71; S, 13.64.
4-(3-chloro-4-fluoro-phenylsulfanyl)-azetidin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
56%
With sodium hydrogencarbonate; In water; acetone; at 20℃; for 12h;Inert atmosphere;
General procedure: Synthesis of compounds 2-28 was performed using procedures adapted from Grimm and co-workers20 and Wasserman et al.21 To a solution of 4-acetoxy-2-azetidinone 1 (1 g; 8 mmol in 50 ml acetone/water, 3:2) 1.05 mol equiv of thiophenols, phenol or benzeneselenol, respectively, were added. Sodium bicarbonate (4 mol equiv) was added and the mixture was stirred vigorously (12 h; closed round bottom flask). Sodium chloride was added to the solution until two layers were formed. The mixture was then filtered and extracted (EtOAc; 3×50 ml). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude product was purified by a variety of methods (preparative HPLC; flash chromatography; and/or recrystallization). 5.1.1.9 4-(3-Chloro-4-fluoro-phenylsulfanyl)-azetidin-2-one (10) The product was purified by recrystallization in ethyl acetate/hexanes to give white crystals (56%) with mp 97-98 C. 1H NMR (400 MHz, CDCl3): δ 7.57 (1H, dd, J = 0.5, 2.5), 7.39 (1H, dd, J = 2.2, 8.9), 7.20 (1H, ddd, J = 0.5, 5.1, 8.6), 6.28 (1H, br s), 4.99 (1H, dd, J = 2.3, 4.9), 3.42 (1H, ddd, J = 2.3, 7.8, 15.4), 2.90 (1H, ddd, J = 1.2, 7.8, 15.8); 13C NMR (100 MHz, CDCl3) δ 165.54, 159.99, 136.29, 134.31, 130.82, 127.34, 121.99, 117.46, 54.58, 45.47; IR (neat) νmax (C=O) 1761.81 cm-1 Anal. Calcd for C9H7ClFNOS: C, 46.66; H, 3.05; Cl, 15.30; F, 8.20; N, 6.05; O, 6.91; S, 13.84. Found: C, 46.57; H, 3.28; Cl, 15.41; F, 8.27; N, 6.28; O, 6.86; S, 13.76.
4-(2,4-dichloro-phenylsulfanyl)-azetidin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
50%
With sodium hydrogencarbonate In water; acetone at 20℃; for 12h; Inert atmosphere;
10 5.1.1. General procedure for synthesis of β-lactams containing aromatic thiols, phenol and benzeneselenol
General procedure: Synthesis of compounds 2-28 was performed using procedures adapted from Grimm and co-workers20 and Wasserman et al.21 To a solution of 4-acetoxy-2-azetidinone 1 (1 g; 8 mmol in 50 ml acetone/water, 3:2) 1.05 mol equiv of thiophenols, phenol or benzeneselenol, respectively, were added. Sodium bicarbonate (4 mol equiv) was added and the mixture was stirred vigorously (12 h; closed round bottom flask). Sodium chloride was added to the solution until two layers were formed. The mixture was then filtered and extracted (EtOAc; 3×50 ml). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude product was purified by a variety of methods (preparative HPLC; flash chromatography; and/or recrystallization). 5.1.1.10 4-(2,4-Dichloro-phenylsulfanyl)-azetidin-2-one (11) The product was purified by recrystallization in ethyl acetate/hexanes to give white crystals (50%) yield with mp 143-144 °C. 1H NMR (400 MHz, CDCl3): δ 7.53 (1H, dd, J = 0.5, 2.2), 7.43 (1H, dd, J = 2.2, 8.3), 7.29 (2H, dd, J = 0.5, 8.5), 6.32 (1H, br s), 5.70 (1H, dd, J = 2.3, 4.9), 3.50 (1H, ddd, J = 1.9, 8.5, 15.7), 3.02 (1H, ddd, J = 1.5, 7.9, 15.5); 13C NMR (100 MHz, CDCl3) δ 165.32, 138.25, 135.49, 135.20, 130.35, 129.65, 127.97, 53.90, 46.02; IR (neat) νmax (C=O) 1683.76 cm-1. Anal. Calcd for C9H7Cl2NOS: C, 43.57; H, 2.84; Cl, 28.57; N, 5.65; O, 6.45; S, 12.92. Found: C, 43.77; H, 2.98; Cl, 28.73; N, 5.57; O, 6.37; S, 12.84.
4-((2-(trifluoromethyl)phenyl)thio)azetidin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
90%
With sodium hydrogencarbonate In water; acetone at 20℃; for 12h; Inert atmosphere;
12 5.1.1. General procedure for synthesis of β-lactams containing aromatic thiols, phenol and benzeneselenol
General procedure: Synthesis of compounds 2-28 was performed using procedures adapted from Grimm and co-workers20 and Wasserman et al.21 To a solution of 4-acetoxy-2-azetidinone 1 (1 g; 8 mmol in 50 ml acetone/water, 3:2) 1.05 mol equiv of thiophenols, phenol or benzeneselenol, respectively, were added. Sodium bicarbonate (4 mol equiv) was added and the mixture was stirred vigorously (12 h; closed round bottom flask). Sodium chloride was added to the solution until two layers were formed. The mixture was then filtered and extracted (EtOAc; 3×50 ml). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude product was purified by a variety of methods (preparative HPLC; flash chromatography; and/or recrystallization). 5.1.1.12 4-((2-(Trifluoromethyl)phenyl)thio)azetidin-2-one (13) The product was purified by recrystallization in ethyl acetate/hexanes to give a yellow-white powder (90%) with mp 81-82 °C. 1H NMR (400 MHz, CDCl3): δ 7.75 (1H, d, J = 7.6), 7.62 (1H, dd, J = 1.3, 7.5), 7.56 (1H, dd, J = 1.5, 7.8), 7.47 (1H, d, J = 7.1), 6.91 (1H, s), 5.03 (1H, dd, J = 2.3, 4.9), 3.44 (1H, ddd, J = 1.8, 7.9, 15.7), 2.95 (1H, ddd, J = 1.6, 7.9, 15.7); 13C NMR (100 MHz, CDCl3) δ 166.26, 135.88, 132.63, 131.42, 128.80, 127.47, 55.05, 45.99; IR (neat) νmax (C=O) 1766 cm-1. Anal. Calcd for C10H8F3NOS: C, 48.58; H, 3.26; N, 5.67. Found: C, 48.73; H, 3.39; N, 5.83.
4-((3-(trifluoromethyl)phenyl)thio)azetidin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
83%
With sodium hydrogencarbonate In water; acetone at 20℃; for 12h; Inert atmosphere;
13 5.1.1. General procedure for synthesis of β-lactams containing aromatic thiols, phenol and benzeneselenol
General procedure: Synthesis of compounds 2-28 was performed using procedures adapted from Grimm and co-workers20 and Wasserman et al.21 To a solution of 4-acetoxy-2-azetidinone 1 (1 g; 8 mmol in 50 ml acetone/water, 3:2) 1.05 mol equiv of thiophenols, phenol or benzeneselenol, respectively, were added. Sodium bicarbonate (4 mol equiv) was added and the mixture was stirred vigorously (12 h; closed round bottom flask). Sodium chloride was added to the solution until two layers were formed. The mixture was then filtered and extracted (EtOAc; 3×50 ml). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude product was purified by a variety of methods (preparative HPLC; flash chromatography; and/or recrystallization). 5.1.1.13 4-((3-(Trifluoromethyl)phenyl)thio)azetidin-2-one (14) The product was purified by recrystallization in ethyl acetate/hexanes to give white crystals (83%) with mp 73-75 °C. 1H NMR (400 MHz, CDCl3): δ 7.72 (1H, d, J = 1.9), 7.67 (1H, dd, J = 1.8, 9.2), 7.62 (1H, dd, J = 7.7, 7.9), 7.51 (1H, dd, J = 1.9, 7.7), 6.80 (1H, s), 5.07 (1H, dd, J = 2.3, 4.9), 3.45 (1H, ddd, J = 1.9, 8.5, 15.7), 2.92 (1H, ddd, J = 1,6, 7.9, 15.7); 13C NMR (100 MHz, CDCl3): δ 166.39, 136.32, 133.41, 131.95 (1C, q, J = 0.33), 130.03, 129.75 (1C, q, J = 0.03), 125.43 (1C, q, J = 0.03), 54.38, 45.83; IR (neat) νmax (C=O) 1766 cm-1. Anal. Calcd for C10H8F3NOS: C, 48.58; H, 3.26; N, 5.67. Found: C, 48.65; H, 3.09; N, 5.63.
4-((4-(trifluoromethyl)phenyl)thio)azetidin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
81%
With sodium hydrogencarbonate In water; acetone at 20℃; for 12h; Inert atmosphere;
14 5.1.1. General procedure for synthesis of β-lactams containing aromatic thiols, phenol and benzeneselenol
General procedure: Synthesis of compounds 2-28 was performed using procedures adapted from Grimm and co-workers20 and Wasserman et al.21 To a solution of 4-acetoxy-2-azetidinone 1 (1 g; 8 mmol in 50 ml acetone/water, 3:2) 1.05 mol equiv of thiophenols, phenol or benzeneselenol, respectively, were added. Sodium bicarbonate (4 mol equiv) was added and the mixture was stirred vigorously (12 h; closed round bottom flask). Sodium chloride was added to the solution until two layers were formed. The mixture was then filtered and extracted (EtOAc; 3×50 ml). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude product was purified by a variety of methods (preparative HPLC; flash chromatography; and/or recrystallization). 5.1.1.14 4-((4-(Trifluoromethyl)phenyl)thio)azetidin-2-one (15) The product was purified by recrystallization in ethyl acetate/hexanes to give white crystals (81%) with mp 95-96.5 °C. 1H NMR (400 MHz, CDCl3): δ 7.61 (2H, doublet, J = 8.2), 7.51 (2H, doublet, J = 8.1), 7.01 (1H, singlet), 5.11 (1H, dd, J = 2.3, 4.9), 3.47 (1H, ddd, J = 1.9, 3.0, 8.4), 2.95 (1H, ddd, J = 0.8, 1.4, 11.7); 13C NMR (100 MHz, CDCl3) δ 166.43, 137.57, 131.75, 130.13 (1C, q, J = 0.33), 126.34, 123.79, 53.78, 45.91; IR (neat) νmax (C=O) 1764 cm-1. Anal. Calcd for C10H8F3NOS: C, 48.58; H, 3.26; N, 5.67. Found: C, 48.83; H, 3.29; N, 5.53.
4-((3,5-Bis(trifluoromethyl)phenyl)thio)azetidin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
79%
With sodium hydrogencarbonate; In water; acetone; at 20℃; for 12h;Inert atmosphere;
General procedure: Synthesis of compounds 2-28 was performed using procedures adapted from Grimm and co-workers20 and Wasserman et al.21 To a solution of 4-acetoxy-2-azetidinone 1 (1 g; 8 mmol in 50 ml acetone/water, 3:2) 1.05 mol equiv of thiophenols, phenol or benzeneselenol, respectively, were added. Sodium bicarbonate (4 mol equiv) was added and the mixture was stirred vigorously (12 h; closed round bottom flask). Sodium chloride was added to the solution until two layers were formed. The mixture was then filtered and extracted (EtOAc; 3×50 ml). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude product was purified by a variety of methods (preparative HPLC; flash chromatography; and/or recrystallization). 5.1.1.15 4-((3,5-Bis(trifluoromethyl)phenyl)thio)azetidin-2-one (16) The product was purified by recrystallization in ethyl acetate/hexanes to give white crystals (79%) with mp 77-79 C. 1H NMR (400 MHz, CDCl3): delta 7.88 (2H, dd, J = 2.0, 8.3), 7.86 (2H, dd, J = 1.9, 8.3), 6.46 (1H, s), 5.17 (1H, dd, J = 2.3, 4.9), 3.55 (1H, ddd, J = 2.4, 8.3, 15.7), 3.00 (1H, ddd, J = 1.6, 7.9, 15.7); 13C NMR (100 MHz, CDCl3) delta 166.04, 135.93, 132.77 (1C, q, J = 0.33), 132.11, 124.30, 122.11, 121.59, 54.22, 46.04; IR (neat) numax (C=O) 1771 cm-1. Anal. Calcd for C11H7F6NOS: C, 41.91; H, 2.24; N, 4.44. Found: C, 41.83; H, 2.08; N, 4.43.
4-(2-methoxy-phenylsulfanyl)-azetidin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
87%
With sodium hydrogencarbonate; In water; acetone; at 20℃; for 12h;Inert atmosphere;
General procedure: Synthesis of compounds 2-28 was performed using procedures adapted from Grimm and co-workers20 and Wasserman et al.21 To a solution of 4-acetoxy-2-azetidinone 1 (1 g; 8 mmol in 50 ml acetone/water, 3:2) 1.05 mol equiv of thiophenols, phenol or benzeneselenol, respectively, were added. Sodium bicarbonate (4 mol equiv) was added and the mixture was stirred vigorously (12 h; closed round bottom flask). Sodium chloride was added to the solution until two layers were formed. The mixture was then filtered and extracted (EtOAc; 3×50 ml). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude product was purified by a variety of methods (preparative HPLC; flash chromatography; and/or recrystallization). 5.1.1.16 4-(2-Methoxy-phenylsulfanyl)-azetidin-2-one (17) The product was purified by recrystallization in hexane/ethyl acetate to give a white solid (87%) with mp 106-107 C. 1H NMR (400 MHz, CDCl3): delta 7.43-6.88 (4H, m), 6.75 (1H, br s), 4.86 (1H, dd, J = 2.3, 4.9), 3.80 (3H, s), 3.28 (1H, ddd, J = 1.8, 8.5, 15.7), 2.93 (1H, ddd, J = 1.4, 8.5, 15.8); 13C NMR (100 MHz, CDCl3) delta 166.56, 160.74, 136.93, 120.82, 114.96, 55.54, 54.90, 44.99; IR (neat) numax (C=O) 1760 cm-1. Anal. Calcd for C10H11NO2S: C, 57.39; H, 5.30; N, 6.69. Found: C, 57.37; H, 5.19; N, 6.67.
4-(3-methoxy-phenylsulfanyl)-azetidin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
75%
With sodium hydrogencarbonate In water; acetone at 20℃; for 12h; Inert atmosphere;
17 5.1.1. General procedure for synthesis of β-lactams containing aromatic thiols, phenol and benzeneselenol
General procedure: Synthesis of compounds 2-28 was performed using procedures adapted from Grimm and co-workers20 and Wasserman et al.21 To a solution of 4-acetoxy-2-azetidinone 1 (1 g; 8 mmol in 50 ml acetone/water, 3:2) 1.05 mol equiv of thiophenols, phenol or benzeneselenol, respectively, were added. Sodium bicarbonate (4 mol equiv) was added and the mixture was stirred vigorously (12 h; closed round bottom flask). Sodium chloride was added to the solution until two layers were formed. The mixture was then filtered and extracted (EtOAc; 3×50 ml). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude product was purified by a variety of methods (preparative HPLC; flash chromatography; and/or recrystallization). 5.1.1.17 4-(3-Methoxy-phenylsulfanyl)-azetidin-2-one (18) The product was purified on a silica gel column (hexanes/ethyl acetate, 1:1; v/v) to give yellow oil in 75% yield. 1H NMR (400 MHz, CDCl3): δ 7.29-6.87 (4H, m), 6.07 (1H, br s), 5.03 (1H, dd, J = 2.3, 4.9), 3.81 (3H, s), 3.39 (1H, ddd, J = 2.4, 7.9, 15.7), 2.91 (1H, dd, J = 1.4, 7.9, 15.7); 13C NMR (100 MHz, CDCl3) δ 169.99, 160.01, 133.17, 130.30, 125.02, 118.24, 114.22, 55.46, 54.22, 45.41; IR (neat) νmax (C=O) 1756 cm-1. Anal. Calcd for C10H11NO2S: C, 57.39; H, 5.30; N, 6.69. Found: C, 57.25; H, 5.34; N, 6.52.
4-(2,5-dimethoxy-phenylsulfanyl)-azetidin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
51%
With sodium hydrogencarbonate; In water; acetone; at 20℃; for 12h;Inert atmosphere;
General procedure: Synthesis of compounds 2-28 was performed using procedures adapted from Grimm and co-workers20 and Wasserman et al.21 To a solution of 4-acetoxy-2-azetidinone 1 (1 g; 8 mmol in 50 ml acetone/water, 3:2) 1.05 mol equiv of thiophenols, phenol or benzeneselenol, respectively, were added. Sodium bicarbonate (4 mol equiv) was added and the mixture was stirred vigorously (12 h; closed round bottom flask). Sodium chloride was added to the solution until two layers were formed. The mixture was then filtered and extracted (EtOAc; 3×50 ml). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude product was purified by a variety of methods (preparative HPLC; flash chromatography; and/or recrystallization). 5.1.1.19 4-(2,5-Dimethoxy-phenylsulfanyl)-azetidin-2-one (20) The product was purified by recrystallization in hexanes/ethyl acetate to give a white solid (51%) with mp 116-118 C. 1H NMR (400 MHz, CDCl3): δ 7.28-6.87 (4H, m), 6.46 (1H, br s), 5.01 (1H, dd, J = 2.3, 4.9), 3.78 (3H, s), 3.41 (1H, ddd, J = 2.4, 8.8, 15.7), 3.86 (3H, s), 2.98 (1H, ddd, J = 2.0, 8.8, 15.7); 13C NMR (100 MHz, CDCl3) δ 166.26, 153.59, 153.19, 120.93, 120.13, 114.78, 112.22, 56.44, 55.83, 53.88, 45.73; IR (neat) νmax (C=O) 1760 cm-1. Anal. Calcd for C11H13NO3S: C, 55.21; H, 5.48; N, 5.85. Found: C, 54.92; H, 5.36; N, 5.81.13.
4-(4-trifluoromethyl-phenoxy)-azetidin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
78%
With sodium hydrogencarbonate In water; acetone at 20℃; for 12h; Inert atmosphere;
25 5.1.1. General procedure for synthesis of β-lactams containing aromatic thiols, phenol and benzeneselenol
General procedure: Synthesis of compounds 2-28 was performed using procedures adapted from Grimm and co-workers20 and Wasserman et al.21 To a solution of 4-acetoxy-2-azetidinone 1 (1 g; 8 mmol in 50 ml acetone/water, 3:2) 1.05 mol equiv of thiophenols, phenol or benzeneselenol, respectively, were added. Sodium bicarbonate (4 mol equiv) was added and the mixture was stirred vigorously (12 h; closed round bottom flask). Sodium chloride was added to the solution until two layers were formed. The mixture was then filtered and extracted (EtOAc; 3×50 ml). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude product was purified by a variety of methods (preparative HPLC; flash chromatography; and/or recrystallization). 5.1.1.25 4-(4-Trifluoromethyl-phenoxy)-azetidin-2-one (26) The product was purified by recrystallization in hexanes/ethyl acetate to give a white powder (78%) with mp 95-98 °C. 1H NMR (400 MHz, CDCl3): δ 7.54 (2H, dd, J = 1.9, 8.7), 6.87 (2H, dd, J = 2.5, 8.6), 6.53 (1H, br s), 5.67 (1H, dd, J = 2.3, 5.0), 3.35 (1H, ddd, J = 1.4, 1.6, 15.0), 3.07 (1H, d, J = 1.6, 3.9, 15.1); 13C NMR (100 MHz, CDCl3) δ 166.46, 158.37, 127.36, 125.11, 124.78, 115.43, 76.23, 46.18; IR (neat) νmax (C=O) 1780 cm-1. Anal. Calcd for C10H8F3NO2: C, 51.96; H, 3.49; N, 6.06. Found: C, 51.91; H, 3.41; N, 5.97.
With sodium hydrogencarbonate In water; acetone at 20℃; for 12h; Inert atmosphere;
26 5.1.1. General procedure for synthesis of β-lactams containing aromatic thiols, phenol and benzeneselenol
General procedure: Synthesis of compounds 2-28 was performed using procedures adapted from Grimm and co-workers20 and Wasserman et al.21 To a solution of 4-acetoxy-2-azetidinone 1 (1 g; 8 mmol in 50 ml acetone/water, 3:2) 1.05 mol equiv of thiophenols, phenol or benzeneselenol, respectively, were added. Sodium bicarbonate (4 mol equiv) was added and the mixture was stirred vigorously (12 h; closed round bottom flask). Sodium chloride was added to the solution until two layers were formed. The mixture was then filtered and extracted (EtOAc; 3×50 ml). The combined organic layers were dried over MgSO4 and concentrated under vacuum. The crude product was purified by a variety of methods (preparative HPLC; flash chromatography; and/or recrystallization). 5.1.1.26 4-Phenylselanyl-azetidin-2-one (27) The product was purified on silica gel (hexanes/ethyl acetate 1:1; v/v) to afford the compound as white crystals (50%) with mp 78-80 °C. 1H NMR (400 MHz, CDCl3): δ 7.35-7.89 (5H, m), 6.33 (1H, br s), 5.14 (1H, dd, J = 2.3, 4.9), 3.45 (1H, ddd, J = 1.70, 7.8, 14.8), 2.97 (1H, ddd, J = 1.6, 7.8, 15.6); 13C NMR (100 MHz, CDCl3): δ 165.91, 135.79, 131.52, 129.52, 129.23, 127.76, 47.29, 46.46; IR (neat) νmax (C=O) 1749.95 cm-1. Anal. Calcd for C9H9NOSe: C, 47.80; H, 4.01; N, 6.19; O, 7.07; Se, 34.92. Found: C, 47.92; H, 4.21; N, 6.39; O, 7.27; Se, 34.89
4-oxo-1-(propylthio)azetidin-2-yl acetate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
66%
Stage #1: Dipropyl disulfide With sulfuryl dichloride In dichloromethane at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: 4-acetoxy azetidinone With triethylamine In dichloromethane for 4h; Inert atmosphere; Reflux;
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