[ CAS No. 930-21-2 ] {[proInfo.proName]}

Name: 930-21-2|Azetidin-2-one|97%
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Quality Control of [ 930-21-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 930-21-2 ]

Product Details of [ 930-21-2 ]

CAS No. :	930-21-2	MDL No. :	MFCD00013328
Formula :	C₃H₅NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MNFORVFSTILPAW-UHFFFAOYSA-N
M.W :	71.08	Pubchem ID :	136721
Synonyms :

Calculated chemistry of [ 930-21-2 ]

Physicochemical Properties

Num. heavy atoms :	5
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.67
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	21.34
TPSA :	29.1 Å²

Pharmacokinetics

GI absorption :	Low
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) :	-7.27 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.84
Log Po/w (XLOGP3) :	-0.75
Log Po/w (WLOGP) :	-0.87
Log Po/w (MLOGP) :	0.01
Log Po/w (SILICOS-IT) :	0.91
Consensus Log Po/w :	0.03

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	0.19
Solubility :	111.0 mg/ml ; 1.56 mol/l
Class :	Highly soluble
Log S (Ali) :	0.62
Solubility :	294.0 mg/ml ; 4.13 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.51
Solubility :	22.1 mg/ml ; 0.31 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 930-21-2 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	3263
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 930-21-2 ]

* 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 [ 930-21-2 ]
Downstream synthetic route of [ 930-21-2 ]

[ 930-21-2 ] Synthesis Path-Upstream 1~8

1
[ 930-21-2 ]
[ 615-36-1 ]
[ 5755-07-7 ]
[ 682341-17-9 ]

Reference： [1] Journal of the American Chemical Society, 2004, vol. 126, # 11, p. 3529 - 3533

2
[ 930-21-2 ]
[ 615-43-0 ]
[ 5755-07-7 ]
[ 682341-17-9 ]

Reference： [1] Journal of the American Chemical Society, 2004, vol. 126, # 11, p. 3529 - 3533

3
[ 930-21-2 ]
[ 30924-93-7 ]
[ 81721-87-1 ]

Yield	Reaction Conditions	Operation in experiment
20%	With dmap; n-butyllithium; dicyclohexyl-carbodiimide In tetrahydrofuran; dichloromethane; ethyl acetate	Intermediate 7b To a stirring solution of azetidin-2-one (36 mg, 0.5 mmol) in 5 mL anhydrous THF was added n-BuLi (1.6 M, 0.31 mL) at -78° C. The solution was stirred for 0.5 h at -78° C. and warmed up to RT. This solution was then transferred into a stirred solution of (S)-5-(benzyloxy)-4-(tert-butoxycarbonylamino)-5-oxopentanoic acid (0.25 g, 0.75 mmol) and DCC (0.16 g, 0.75 mmol) in 5 mL dichloromethane (pre stirred for 10 minutes). To the mixture was then added DIEA (0.55 mmol) and DMAP (0.2 mmol) and the solution was stirred at RT for 10 hours. The solvent was removed and the crude was purified by flash column chromatography on silica gel with heptane/EtOAc (1:1) to afford 30 mg of white solid (20percent) as intermediate 7b. LC-MS: 291.1 (ES+, M-Boc).

Reference： [1] Patent: US2011/269244, 2011, A1, . Location in patent: Page/Page column

4
[ 930-21-2 ]
[ 64-19-7 ]
[ 28562-53-0 ]

Reference： [1] Tetrahedron Letters, 1991, vol. 32, # 42, p. 5991 - 5994
[2] Tetrahedron Letters, 1991, vol. 32, # 19, p. 2145 - 2148
[3] Tetrahedron Letters, 1988, vol. 29, # 12, p. 1409 - 1412

5
[ 930-21-2 ]
[ 28562-53-0 ]

Yield	Reaction Conditions	Operation in experiment
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°, 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,

6
[ 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.

Reference： [1] Patent: US5191076, 1993, A,

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
[ 930-21-2 ]
[ 28562-53-0 ]

Reference： [1] Patent: US5204460, 1993, A,

[ 930-21-2 ] Synthesis Path-Downstream 1~18

1
[ 930-21-2 ]
[ 3017-70-7 ]
1-(1,2-dimethyl-1-propenyl)-azetidin-2-one [ No CAS ]

Reference： [1]Organic Letters,2003,vol. 5,p. 3667 - 3669

2
[ 930-21-2 ]
[ 615-43-0 ]
[ 5755-07-7 ]
[ 682341-17-9 ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 3529 - 3533

3
[ 930-21-2 ]
[ 3959-05-5 ]
2,3,5,6-tetrahydro-1H-benzo[b][1,5]diazocin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With copper(l) iodide; potassium carbonate In toluene at 110℃; for 24h;

Reference： [1]Klapars, Artis; Parris, Sean; Anderson, Kevin W.; Buchwald, Stephen L. [Journal of the American Chemical Society, 2004, vol. 126, # 11, p. 3529 - 3533]

4
[ 930-21-2 ]
[ 68856-96-2 ]
[ 350245-17-9 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 9687 - 9693
[2]Organic letters,2001,vol. 3,p. 1813 - 1815

5
[ 930-21-2 ]
[ 615-36-1 ]
[ 5755-07-7 ]
[ 682341-17-9 ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 3529 - 3533

6
[ 930-21-2 ]
[ 6602-54-6 ]
[ 1003023-85-5 ]

Yield	Reaction Conditions	Operation in experiment
28.9%	With caesium carbonate In toluene at 90℃; for 16h;	27.A An oven dried round bottom flask was purged with argon then charged with 2- chloronicotinonitrile (277 mg, 2.0 mmol), azetidin-2-one (142 mg, 2.0 mmol), Palladium dibenzylideneacetone (115 mg, 0.1 mmol), Xantphos (174 mg, 0.3 mmol) and cesium carbonate (1.3g, 4.0 mmol) followed by toluene (10 mL). The suspension was heated at 90 0C for 16 hours (overnight). After cooling, the yellow suspension was filtered through a pad of celite and the filter cake was rinsed with CH2Cl2. The filtrate was concentrated and subjected to flash chromatography on silica gel using 5% MeOH:95% CH2Cl2 to give a yellow solid. Yield: 100 mg (28.9%) 1H-NMR (400 MHz, DMSO-d6) δ 8.65 (dd, IH, J = 1.6 Hz, 3.2 Hz), 8.30 (dd, IH, J = 6.0 Hz, 2.0 Hz), 7.35 (m, IH), 3.88 (t, 2H, J = 5.2 Hz), 3.18 (t, 2H, J = 5.2 Hz).
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 90℃;

Reference： [1]Current Patent Assignee: DEBIOPHARM INTERNATIONAL SA - WO2008/9122, 2008, A1 Location in patent: Page/Page column 120
[2]Location in patent: scheme or table Ramnauth, Jailall; Surman, Mathew D.; Sampson, Peter B.; Forrest, Bryan; Wilson, Jeff; Freeman, Emily; Manning, David D.; Martin, Fernando; Toro, Andras; Domagala, Megan; Awrey, Donald E.; Bardouniotis, Elias; Kaplan, Nachum; Berman, Judd; Pauls, Henry W. [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 18, p. 5359 - 5362]

7
[ 930-21-2 ]
4-triphenyl methyl mercaptoazetidinone [ No CAS ]
H₂ S_.triethyl amine [ No CAS ]
[ 3740-52-1 ]
[ 4024-81-1 ]
Sodium 2-(2'-Aminophenyl)methylpenem-3-carboxylate [ No CAS ]
thioacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With sodium hydrogencarbonate; triethylamine In dichloromethane	45 Sodium 2-(2'-Aminophenyl)methylpenem-3-carboxylate STR477 EXAMPLE 45 Sodium 2-(2'-Aminophenyl)methylpenem-3-carboxylate STR477 A cold (dry ice-acetone bath) methylene chloride (40 cc) solution of H2 S.triethyl amine (from 1.45 g, 2 cc 14.4 mmoles of triethylamine) was treated (fast) with a methylene chloride (20 cc) solution of acid chloride 1 (from 2 g, 11.0 mmoles of o-nitrophenylacetic acid) for 45 min under nitrogen atmosphere. The mixture was then diluted with ether and washed with 10% HCl, water and brine. It was dried over MgSO4 (1.69 g, 77.5%). δ(ppm, CDCl3) 8.27-8.08, 7.87-7.30 (m, 4H, aromatic-H), 4.90 (1H, b.s.,SH), 4.33 (2H, s, CH2). νCO (neat) 1705, νSH 2565, νNO2 1525. STR478 A cold (0° C.) THF-water (25 cc-200 cc) solution of thioacid 2 (7.92 g, 40.2 mmoles) was treated with NaHCO3 (3.38 g, 40.2 mmoles) for 5 min under nitrogen atmosphere. The resulting solution was treated with an aqueous (50 cc) solution of azetidinone 3 (5.18 g, 40.1 mmoles). The mixture was stirred for 15 min at 0° and then allowed to react 4 h at room temperature. The solution was extracted with CH2 Cl2 (4*50 cc). The methylene chloride extracts were combined, washed with 10% aqueous HCl, water and brine and dried over MgSO4. The residue obtained upon solvent evaporation was passed through a silica gel (45 g) column (benzene-ether). Thioacetate 4 was obtained in 57% yield. (4.00 g, m.p.: 72°-72.5°). Anal. calc'd for C11 H10 N2 O4 S: C, 49.62; H, 3.78; N, 10.52; S, 12.04. Found: C, 49.55; H, 3.42; N, 10.74; S, 12.29. δ(ppm, CDCl3) 8.28-8.07, 7.85-7.32 (4H, m, aromatic-H), 6.93 (1H, bs, N-H), 5.22 (1H, dd, J3-4 trans=2.8, J3-4 cis =5, H-3), 4.28 (2H, s, CH2 CO), 3.45 (1H, ddd, J4-3 gem =15.2, J4-3 cis =5, J4-NH =2.2, H-4), 2.88 (1H, J4-3 gem =15.2, J4-3 trans =2.8, J4-NH =1.2, H-4). νc=o (CHCl3), 1777, 1695, νNO2 1530, νNH 3420. STR479

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US4272437, 1981, A

8
[ 930-21-2 ]
[ 381233-96-1 ]
[ 941604-89-3 ]

Yield	Reaction Conditions	Operation in experiment
82.6%	With caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene;tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 90℃; for 19h;	An argon purged round bottom flask was charged with 5-bromo-3-iodopyridin-2- amine (150 mg, 0.5 mmol), azetidin-2-one (36 mg, 0.5 mmol), tris-dibenzylideneacetone dipalladium (23 mg, 0.05 mmol), Xantphos (43 mg, 0.075 mmol) and cesium carbonate (326 mg, 1.0 mmol) followed by toluene (10 mL). The suspension was heated at 900C for 19 hours (overnight). After cooling, the mixture was filtered through a pad of celite and the filter cake was rinsed with 5 mL CH2Cl2- The filtrate was concentrated and subjected to flash chromatography on silica gel using 2.5% MeOH:97.5 % CH2Cl2 to give a yellow solid. Yield: 100 mg (82.6 %). 1H NMR (300 MHz, DMSOd6) delta 7.87 (d, IH, J = 2.4Hz), 7.45 (d, IH, J = 2.4Hz), 6.53 (br s, 2H), 3.67 (t, 2H, J = 4.4 Hz), 3.03(t, 2H, J = 4.6 Hz); ESI MS m/z 242 and 244 [C8H8N3OBr+ H]+
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; at 90℃; for 19h;	(i) Azetidin-2-one, Pd2(dba)3, Xantphos, Cs2C03, Toluene, 90C, 19h; (ii) Ti(OPr)4, Toluene, 110C, 15h; (iii)Pd(OAc)2, P(0-tolyl)3, DIPEA, Propionitrile:D F,100-l 10C, 16h; (Ref. for step-(i-ii): WO2007067416)

Reference： [1]Patent: WO2007/67416,2007,A2 .Location in patent: Page/Page column 65; 141
[2]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5359 - 5362
[3]Patent: WO2013/80222,2013,A1 .Location in patent: Page/Page column 78

9
[ 930-21-2 ]
[ 14871-92-2 ]
[Pd(C₃H₄NO)2(C₁₀H₈N₂)]*2H₂O [ No CAS ]

Reference： [1]Polyhedron,1997,vol. 16,p. 1662 - 1678

10
[ 930-21-2 ]
[ 7436-90-0 ]
[ 1188522-06-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In toluene at 80℃; for 24h; Inert atmosphere; regioselective reaction;
84%	With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In toluene at 80℃; for 24h;

Reference： [1]Coste, Alexis; Couty, Francois; Evano, Gwilherm [Organic Letters, 2009, vol. 11, # 19, p. 4454 - 4457]
[2]Jouvin, Kevin; Coste, Alexis; Bayle, Alexandre; Legrand, Frederic; Karthikeyan, Ganesan; Tadiparthi, Krishnaji; Evano, Gwilherm [Organometallics, 2012, vol. 31, # 22, p. 7933 - 7947]

11
[ 930-21-2 ]
[ 540-38-5 ]
[ 1309606-48-1 ]

Yield	Reaction Conditions	Operation in experiment
31%	With copper(l) iodide; potassium carbonate In toluene at 18 - 140℃; for 20h; Inert atmosphere; Sealed;

Reference： [1]Location in patent: experimental part Lange, Jens; Bissember, Alex C.; Banwell, Martin G.; Cade, Ian A. [Australian Journal of Chemistry, 2011, vol. 64, # 4, p. 454 - 470]

12
[ 930-21-2 ]
[ 939-18-4 ]
[ 1335032-85-3 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 5077 - 5088

13
[ 930-21-2 ]
[ 504-88-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With methyltrifluoromethyldioxirane In water at 0℃; for 0.5h;	General procedure: In a typical experiment, a 25-mL round-bottom flask was charged with 6 mL of distilled water and 300 mg (0.79 mmol) of CTAHS. To this solution, 60 mg (0.327 mmol) of 2g were added and the mixture was cooled to 0 °C. Under vigorous stirring, 4.4 mL of a 0.60 M solution of 1b (2.616 mmol) in TFP were rapidly added and the resulting mixture allowed to react until the oxidant was consumed (1.5 h, iodometry). Then, the reaction flask was surmounted with a distillation column equipped with an efficient condenser kept at ca. 0 °C and the TFP was gently distilled off. The resulting residue was cooled to room temperature, saturated with NaCl, then extracted with ethyl acetate (3 × 20 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo. Chromatographic separation (silica gel, ethyl acetate/hexane 2:3) of the residue afforded 32.4 mg of unreacted 2g (0.178 mmol, conv. 46%) and 35.2 mg (0.143 mmol, 95% yield based on the amount of substrate reacted; purity >98%, HPLC).

Reference： [1]Annese, Cosimo; D'Accolti, Lucia; Filardi, Rosella; Tommasi, Immacolata; Fusco, Caterina [Tetrahedron Letters, 2013, vol. 54, # 6, p. 515 - 517]

14
[ 930-21-2 ]
[ 30924-93-7 ]
[ 81721-87-1 ]

Yield	Reaction Conditions	Operation in experiment
20%	With dmap; n-butyllithium; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; ethyl acetate;	Intermediate 7b To a stirring solution of azetidin-2-one (36 mg, 0.5 mmol) in 5 mL anhydrous THF was added n-BuLi (1.6 M, 0.31 mL) at -78 C. The solution was stirred for 0.5 h at -78 C. and warmed up to RT. This solution was then transferred into a stirred solution of (S)-5-(benzyloxy)-4-(tert-butoxycarbonylamino)-5-oxopentanoic acid (0.25 g, 0.75 mmol) and DCC (0.16 g, 0.75 mmol) in 5 mL dichloromethane (pre stirred for 10 minutes). To the mixture was then added DIEA (0.55 mmol) and DMAP (0.2 mmol) and the solution was stirred at RT for 10 hours. The solvent was removed and the crude was purified by flash column chromatography on silica gel with heptane/EtOAc (1:1) to afford 30 mg of white solid (20%) as intermediate 7b. LC-MS: 291.1 (ES+, M-Boc).

Reference： [1]Patent: US2011/269244,2011,A1 .Location in patent: Page/Page column

15
[ 930-21-2 ]
[ 16642-79-8 ]
[ 1024602-82-1 ]

Yield	Reaction Conditions	Operation in experiment
65%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 2h;	Example 1 Summary of Experimental Conditions for the Preparation of Compound 13 [0173] Several routes to generate 13 were explored. In the past, KF on alumina has been employed in several types of transformations to promote a slow deprotonation of the azetidinone, but low conversion to 13 was observed over a 3-day period when this approach was tried (data not shown). Experimental Conditions [0174] RRN 51. A first route to generate 13 employed Cl250 to make the acid chloride 10 and n-BuLi to deprotonate azetidinone 11. In a first flask, acid 9 was treated with Cl2SO to prepare acid chloride 10. Upon reaction completion, excess Cl250 was removed by distillation and the acid chloride was dissolved in THF. In a second flask azetidinone 11 was treated with n-BuLi in THF at the specified temperature. The acid chloride solution prepared in the first flask was added to the second flask and the mixture warmed to RT. After aqueous workup, the product was purified by chromatography. 2. The second route to generate 13 employed (COCl)2 to make the acid chloride 10 and LiHMDS to deprotonate azetidinone 11. A similar protocol was employed as for the first route, above. 3. The third route explored used CDI/DIPEA. CU was added to a solution of acid 9 in CH2Cl2. After 1 hr at RT, 2-azetidinone (11) was added and the mixture is stirred at RT for the desired amount of time. 4. The fourth route explored was a combination of T3P and DIPEA. To a solution of acid 9,2-azetidinone 11, and DIPEA in a suitable solvent was added a 50% solution of T3P in EtOAc. The mixture was stirred at the desired temperature for the specified amount of time. Upon reaction completion, an aqueous workup was performed and compound 13 was purified by recrystallization from a suitable solvent. It was found that the preparation of acid chloride 10 using Cl2SO or oxalyl chloride and the subsequent reaction with the anion of 2-azetidinone prepared via deprotonation with BuLi or LiHMDS led to the desired product 13 but generally gave low yield and purity. [0176] The activation of acid 9 with CU was readily achieved, but the subsequent coupling with 2-azetidinone or its anion failed in solvents such as CH2Cl2, THF, and EtOAc, most likely due to the low nucleophilicity of this substrate. [0177] The best results were obtained from the fourth route, using DIPEA/T3P. Example 2 Synthesis of 13 To a solution of <strong>[16642-79-8]3-(4-nitrophenyl)propanoic acid</strong> (9, 440 g, 2.25 mol), 2-azetidinone (11, 240 g, 3.37 mol), and DIPEA (1.46 kg, 11.3 mol) in MeCN (4.4 L) was added a 50% (wt/wt) solution of 1-propanephosphonic acid anhydride (T3P) in EtOAc (2.15 kg, 3.38 mol) over 1 hr while the internal temperature was held at 20-25 C. After the resulting mixture had been stirred at 22 C. for 20 hrs, HPLC analysis showed 0.9% of unreacted 9. [0180] The reaction was concentrated under reduced pressure to about 2 L and the residue was taken up in i-PrOAc (6.6 L) at 30-35 C. The organic layer was washed with 10% aqueous citric acid (4 L). The aqueous layer was back-extracted with i-PrOAc (2.7 L) and to the combined organic extracts was added Darco G-60 (90 g). The mixture was stirred at 25 C. for 4 hrs and filtered through celite. The celite filter was washed with i-PrOAc (0.5 L) and the filtrates were concentrated under reduced pressure to about 1 L. 2-Propanol (2.2 L) was added and the distillation was resumed to a final volume of about 1 L. 2-Propanol (2.2 L) was added and the mixture was cooled to 3 C. and held at this temperature for 1 hr. The solid was filtered and washed with 2-propanol (0.55 L). The wet cake was transferred back to the reactor and dissolved in EtOAc (3.24 L). Darco G-60 (90 g) was added and the mixture was stirred at 25 C. for 2 hrs. The suspension was filtered through celite and the celite pad was washed with EtOAc (0.5 L). The filtrates were concentrated under reduced pressure to about 1 L and 2-propanol (1.4 L) was added. The solution was concentrated to about 1 L and additional 2-propanol (1.4 L) was added. The suspension was cooled to 3 C. and held at this temperature for 1 hr. The solid was filtered, washed with 2-propanol (0.5 L), and dried at 30-35 C. under vacuum for 8 hrs to give 273 g (49%) of 13. [0181] HPLC retention time: 2.68 min. HPLC purity: 98.0% (a/a). Mp: 104-106 C. 1H NMR (400 MHz, DMSO-d6) delta ppm 2.88-3.05 (m, 6H) 3.42 (t, J=5.27 Hz, 2H) 7.44-7.53 (m, 2H) 8.07-8.16 (m, 2H). 13C NMR (100 MHz, DMSO-d6) delta ppm 29.37, 36.05, 36.89, 37.00, 123.83, 130.06, 146.38, 149.49, 166.20, 169.38. MS (ES+): 249 (M+H)+. Example 3

Reference： [1]Patent: US2015/31108,2015,A1 .Location in patent: Paragraph 0173-0181
[2]Organic Process Research and Development,2014,vol. 18,p. 142 - 151

16
[ 930-21-2 ]
[ 5448-43-1 ]
1-quinoxalin-6-yl-azetidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With (PAd₂-DalPhos)NiCl(o-tol); caesium carbonate In 1,4-dioxane at 90℃; for 18h; Inert atmosphere; Glovebox; Sealed tube;

Reference： [1]Lavoie, Christopher M.; MacQueen, Preston M.; Stradiotto, Mark [Chemistry - A European Journal, 2016, vol. 22, # 52, p. 18752 - 18755]

17
[ 930-21-2 ]
[ 57455-06-8 ]
1-(3-(hydroxymethyl)phenyl)azetidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In toluene at 80℃; for 1.5h; Inert atmosphere;	1-(3-(hydroxymethyl)phenyl)azetidin-2-one: CuT (19 mg, 0.10 mmol) andK3P04 (849 mg, 4.00 mmol) were added to a vial which was purged with argon. N, N’dimethylethylenediamine (0.022 mL, 0.2 mmol), 3-(iodophenyl)methanol (468 mg, 2.00 mmol) and 2-azetidinone (171 mg, 2.4 mmol) were then added followed by toluene (2 mL). The reaction mixture was heated to 80 °C for 90 minutes after which it was cooled to room temperature, passed through a short silica plug washing withEtOAc and MeOH, and concentrated. The crude residue was then purified by flash chromatography (eluent: MeOH / DCM) to give the desired product.

Reference： [1]Current Patent Assignee: GILEAD SCIENCES INC - WO2017/7694, 2017, A1 Location in patent: Page/Page column 107; 108

18
[ 930-21-2 ]
[ 3430-26-0 ]
1-(5-bromo-4-methylpyridin-2-yl)azetidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; at 120℃; for 19.5h;Inert atmosphere; Molecular sieve; Sealed tube;	Into a vial was weighed <strong>[3430-26-0]2,5-dibromo-4-methylpyridine</strong> (1.22 g, 4.84 mmol), 2-azetidinone (421 mg, 5.81 mmol), tris(dibenzylideneacetone)dipalladium(0) (111 mg, 0.121 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyxanthene (140 mg, 0.242 mmol), 3 A molecular sieves (600 mg), and cesium carbonate (3.16 g, 9.69 mmol). Under a stream of nitrogen gas, the vessel was charged with anhydrous toluene (16 mL) and the vial was sealed. The reaction mixture was stirred at 120 C. for 19.5 h before cooling to rt. The reaction mixture was filtered through Celite rinsing with dichloromethane. After concentration, the crude residue was purified by flash chromatography (100:0-70:30 heptanes/iPrOAc) to afford the title compound as a white solid (828 mg, 71%); 1H NMR (400 MHz, Chloroform-d) delta 8.31 (s, 1H), 7.66 (s, 1H), 3.77 (dd, J=4.7, 4.7 Hz, 2H), 3.12 (dd, J=4.7, 4.7 Hz, 2H), 2.39 (s, 3H).

Reference： [1]Patent: US2018/282328,2018,A1 .Location in patent: Paragraph 2272; 2273

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[ CAS No. 930-21-2 ] {[proInfo.proName]}

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[ 930-21-2 ] Synthesis Path-Upstream 1~8

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Amides

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Aliphatic Heterocycles

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