[ CAS No. 6305-38-0 ] {[proInfo.proName]}

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Quality Control of [ 6305-38-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 6305-38-0 ]

Product Details of [ 6305-38-0 ]

CAS No. :	6305-38-0	MDL No. :	MFCD00012723
Formula :	C₄H₈BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	182.02	Pubchem ID :	-
Synonyms :	3-Aminooxolan-2-one hydrobromide

Safety of [ 6305-38-0 ]

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

Application In Synthesis of [ 6305-38-0 ]

* 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.

Upstream synthesis route of [ 6305-38-0 ]
Downstream synthetic route of [ 6305-38-0 ]

[ 6305-38-0 ] Synthesis Path-Upstream 1~3

1
[ 6305-38-0 ]
[ 50768-69-9 ]
[ 5061-21-2 ]
[ 497-23-4 ]

Reference： [1] Patent: KR2015/118287, 2015, A, . Location in patent: Paragraph 0095; 0109-0114

2
[ 24424-99-5 ]
[ 6305-38-0 ]
[ 40856-59-5 ]

Reference： [1] Chemistry - A European Journal, 2006, vol. 12, # 15, p. 4121 - 4143
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 19, p. 4755 - 4765

3
[ 6305-38-0 ]
[ 15159-65-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	at 100℃; for 6 h; Inert atmosphere	α-Amino-γ-butyrolactone hydrobromide 1 (1 g, 4.4 mmol) was suspended in acetic acid saturated with hydrogen bromide (~33percent) (8 mL). The suspension was heated to 100 °C for 6 hrs under a nitrogen atmosphere and then allowed to cool over 1 hr in an ice bath. A white precipitate formed. The precipitate was suspended in diethyl ether (anhydrous, 70 mL), the solid collected by vacuum filtration, washed with diethyl ether (40 mL) and dried under high vacuum to give butyric acid 2 as a white solid (1.01 g, 88percent). The 1H NMR spectrum of 2 was consistent with those reported in the literature.1 1H NMR (200 MHz, D2O): δ 2.25 - 2.55 (m, 2H, H3), 3.47 – 3.62 (m, 2H, H4), 4.12 (dd, 1H, J = 6.6, 7 Hz, H2).

Reference： [1] Chemistry - A European Journal, 2013, vol. 19, # 13, p. 4244 - 4248
[2] Journal of Organic Chemistry, 2005, vol. 70, # 17, p. 6757 - 6774
[3] Tetrahedron, 2013, vol. 69, # 5, p. 1576 - 1582

[ 6305-38-0 ] Synthesis Path-Downstream 1~87

1
[ 6305-38-0 ]
[ 76224-60-7 ]
[ 76224-61-8 ]

Reference： [1]Chemistry Letters,1980,p. 1215 - 1218

2
[ 6305-38-0 ]
[ 78553-60-3 ]
[ 79848-46-7 ]

Reference： [1]Chemistry Letters,1981,p. 909 - 912

3
[ 1927-25-9 ]
[ 6305-38-0 ]

Yield	Reaction Conditions	Operation in experiment
81%	With hydrogen bromide;Reflux;	A solution of DL-homoserine (0.31 g, 2.6 mmoles) in 2.4 M hydrobromic acid (5 mL, 12 mmoles, 4.6 eq) was refluxed for 3 h and then stirred overnight. Removal of the solvent afforded a white solid, which was dissolved in ethanol and cooled to give the product as a solid which was collected by filtration and washed with cold ethanol to give 0.384 g (81percent) of the product (A), m.p. 117-119° C. Calcd. for C4H8NO2Br: C, 26.40; H, 4.44; N, 7.70. Found: C, 26.35; H, 4.25; N, 7.51.

Reference： [1]Canadian Journal of Chemistry,2003,vol. 81,p. 937 - 960
[2]Patent: US2003/232820,2003,A1 .Location in patent: Page 9

4
[ 6305-38-0 ]
[ 15159-65-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With hydrogen bromide; acetic acid; at 100℃; for 6h;Inert atmosphere;	alpha-Amino-gamma-butyrolactone hydrobromide 1 (1 g, 4.4 mmol) was suspended in acetic acid saturated with hydrogen bromide (~33%) (8 mL). The suspension was heated to 100 C for 6 hrs under a nitrogen atmosphere and then allowed to cool over 1 hr in an ice bath. A white precipitate formed. The precipitate was suspended in diethyl ether (anhydrous, 70 mL), the solid collected by vacuum filtration, washed with diethyl ether (40 mL) and dried under high vacuum to give butyric acid 2 as a white solid (1.01 g, 88%). The 1H NMR spectrum of 2 was consistent with those reported in the literature.1 1H NMR (200 MHz, D2O): delta 2.25 - 2.55 (m, 2H, H3), 3.47 - 3.62 (m, 2H, H4), 4.12 (dd, 1H, J = 6.6, 7 Hz, H2).

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 4244 - 4248
[2]Journal of Organic Chemistry,2005,vol. 70,p. 6757 - 6774
[3]Tetrahedron,2013,vol. 69,p. 1576 - 1582

5
[ 6305-38-0 ]
[ 142-62-1 ]
N-hexanoyl-L-homoserine lactone [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2005,vol. 53,p. 6262 - 6265

6
[ 875667-97-3 ]
[ 6305-38-0 ]
[ 875668-06-7 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 770 - 788

7
[ 3392-12-9 ]
[ 6305-38-0 ]
[ 602307-60-8 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3926 - 3932

8
[ 199168-31-5 ]
[ 6305-38-0 ]
pentanedioic acid (4-methoxyphenyl)amide (2-oxotetrahydrofuran-3-yl)amide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 2802 - 2803

9
3-hydroxy-6-(4-methoxy-phenylcarbamoyl)-hexanoic acid [ No CAS ]
[ 6305-38-0 ]
3-hydroxyheptanedioic acid 7-[(4-methoxyphenyl)amide] 1-[(2-oxotetrahydrofuran-3-yl)amide] [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 2802 - 2803

10
6-(4-methoxy-phenylcarbamoyl)-3-oxo-hexanoic acid [ No CAS ]
[ 6305-38-0 ]
3-oxoheptanedioic acid 7-[(4-methoxyphenyl)amide] 1-[(2-oxotetrahydrofuran-3-yl)amide] [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 2802 - 2803

11
[ 876760-85-9 ]
[ 6305-38-0 ]
heptanedioic acid (4-methoxyphenyl)amide (2-oxotetrahydrofuran-3-yl)amide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 2802 - 2803

12
[ 933751-05-4 ]
[ 6305-38-0 ]
[ 1004317-59-2 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation of Compound 100; Scheme 70I. a. CDI, DIPEA, MeCN; <n="285"/>Compound 100 was prepared using the same method used to prepare Compound 122, except that Compound 9 was replaced with Compound 68.

Reference： [1]Patent: WO2008/10921,2008,A2 .Location in patent: Page/Page column 257; 283-284

13
[ 6305-38-0 ]
[ 154212-60-9 ]
[ 1004316-93-1 ]

Yield	Reaction Conditions	Operation in experiment
		purified by CombiPlash (eluted with 20-80% EtOAc/hexanes) to give 3.2 g ofCompound 207 as a pale yellow oil. m/z 298.0 (M+H)+.

Reference： [1]Patent: WO2008/10921,2008,A2 .Location in patent: Page/Page column 282-283

14
[ 6305-38-0 ]
[ 124-63-0 ]
N-methanesulfonyl-L-homoserine lactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0℃; for 0.5h;	Preparation 1 (219.8mg ; 1. [21MMOL)] was suspended in DCM (5mL), and Et3N (0.34mL ; 2. [4MMOL)] was added while stirring. The mixture was cooled to [0C,] and [METHANESULFONYL] chloride (210 mg; 1.83 [MMOL)] was added. The mixture was stirred for another 30 min. at [0C.] The reaction mixture was evaporated to dryness and the solid was dissolved in DCM (3mL) and flash chromatographed with the eluent hexan/EtOAc [(1] : 4) to give the title compound. mp: [107-108C.] [[A] D (C] = 9.75mg ; lOmL DCM) [=-48.] [21. 1H] NMR [(D2O)] [8] : 4.42, 4.35, 4.19, 3.05, 2.58, 2.13 ; [13C] NMR [8] : 177.9, 66.9, 52.0, 41.2, 29.5. IR (KBr): 3258,1766, 1354,1144. Elemental analysis : Found (cal) : C: 33.91 (33.51) ; H: 4.82 (5.06) ; N: 7.68 (7.82)

Reference： [1]Patent: WO2003/106445,2003,A1 .Location in patent: Page 29

15
[ 6305-38-0 ]
[ 594-44-5 ]
N-ethanesulfonyl-L-homoserine lactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0℃; for 0.5h;	Preparation 1 (207.7mg ; 1. 14mmol) was suspended in DCM (5mL), and Et3N (0.34mL ; 2. [4MMOL)] was added while stirring. The mixture was cooled to [0C,] and [ETHANESULFONYL] chloride (255.0 mg; 1.98 [MMOL)] was added. The mixture was stirred for another 30 min. at [0C.] The reaction mixture was evaporated to dryness and the solid was dissolved in DCM (3mL) and flash chromatographed with the eluent hexan/EtOAc (1: 2) to give the title compound; mp: [72-73C.] [[A] D (C] = 9.89mg ; lOmL DCM) [=-25.] [28. 1H] NMR [(CI3)] 8 : 5.37, 5.29, 4.43, 4.36, 4.20, 3.22, 2.73, 2.29, 1.41. [13C] NMR 8 : 174.9, 65.6, 52.0, 48.7, 30.7, 8.1. IR [(KBR)] : 3302,1794, 1341,1132 [CM-1.]

Reference： [1]Patent: WO2003/106445,2003,A1 .Location in patent: Page 30

16
[ 2386-60-9 ]
[ 6305-38-0 ]
N-(butylsulfonyl)-L-homoserine lactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With triethylamine; In dichloromethane; at 0℃; for 0.5h;	Preparation 1 (182. [OMG] ; [L.] 0mmol) was suspended in DCM (5mL), and Et3N (0.31 ; 2. [2MMOL)] was added while stirring. The mixture was cooled to [0C,] and 1-butanesulfonyl chloride (210mg; 1. 34mmol) was added. The mixture was stirred for another 30 min. at 0C. DCM (5mL) was added and the solution was washed with HCI (3%, [LOML),] NaHCO3 [ (5%, LOML), AND TWICE WITH NACL (SAT. , LOML). THE ORGANIC LAYER WAS DRIED WITH NA2504,] evaporated to dryness and the solid was dissolved in DCM (3mL) and flash chromatographed in the eluent hexan-EtOAc (3: 2) to give the title compound. mp: 76- [78C.] [[A]] o (c = 9.13mg ; lOmL DCM) [=-21.] [14. 1H] NMR (CDC13) 8 : 5.47, 4.41, 4.33, 4.26, 3.16, 2.68, 2.28, 1.8, 0.92. [13C] NMR 8 : 175.0, 65.5, 54.0, 51.9, 30.4, 25.2, 21.2, 13.4 ; IR (KBr): 3258,1766, 1354,1144 [CM-1.]

Reference： [1]Patent: WO2003/106445,2003,A1 .Location in patent: Page 30, 39

17
[ 88107-02-2 ]
[ 6305-38-0 ]
N-(4-phenylbutane-1-sulfonyl)-L-homoserine lactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0 - 20℃;	A suspension of preparation 10 (14 mg, 0.059 [MMOL)] in SOCS (47 [L,] 0.65 [MMOL)] under argon with a catalytic amount of DMF (-1 muL) was heated close to reflux while stirring for 3 hrs to yield an oil after the solvent was removed. It was dissolved in DCM (1 mL) and transferred drop-wise via syringe to preparation 1 (9.8 mg, 0.054 [MMOL)] dissolved by NEt3 (16 [L,] 0.31 [MMOL)] in DCM [(1] mL). The addition was made at [0C] and under argon and took [1/2] hour. After 3 hrs of stirring the reaction mixture was allowed to warm to ambient temperature and then left overnight. Quenching (H2O) the reaction followed by extraction [(3X30] mL EtOAc), washing the combined organic phases with [H20,] drying [(MGS04)] and filtration provided a yellow oily crude that was purified by flash- chromatography (flash-collector : Biotage; Si02 ; eluent : DCM) to afford the title compound. mp=85-87 [C.] IR (neat): 3313,1774, 1305,1142 [CM-1. 1H] NMR (500 MHz, [CDC13)] 8 : 7.29-7. 16,4. 96,4. 43,4. 30-4.21, 3.15, 2.76-2. 70,2. 66,2. 26-2.18, 1.94-1. 88, 1. [79. 13C] NMR (125 MHz, [CDC13)] 8 : 174.50, 141.35, 128.43, 128.38, 126.01, 65.58, 54.25, 52.136, 35.30, 31.22, 29.81, 23.19.

Reference： [1]Patent: WO2003/106445,2003,A1 .Location in patent: Page 32-33

18
[ 63014-04-0 ]
[ 6305-38-0 ]
N-(3-phenylpropane-1-sulfonyl)-L-homoserine lactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0 - 20℃;	A suspension of preparation 9 (33 mg, 0.16 [MMOL)] in [SOC12] (120 [L,] 1.65 [MMOL)] under argon with a catalytic amount of DMF (1 muL, 0.016 [MMOL)] was heated close to reflux while stirring for 3 hrs to yield an oil after the solvent was removed. It was dissolved in DCM (1 mL) and transferred drop-wise via syringe to preparation 1 (26.5 mg, 0.15 [MMOL)] dissolved by NEt3 (43 [PL,] 0.31 [MMOL)] in DCM (2 mL). The addition was made at [0C] and under argon and took [1/2] hour. After 4 hrs of stirring the reaction mixture was allowed to warm to ambient temperature and then left overnight. Quenching (H2O) the reaction followed by extraction (3x10 mL EtOAc), washing the combined organic phases with [H2O,] drying [(MGS04)] and filtration provided a crude product that was purified by flash-chromatography (flash-collector : Biotage; [SI02] ; eluent : 2% [MEOH] in DCM) to yield the title compound. mp=73-75 [C] ; IR (neat) =3348, 1782,1315, 1148 cm-1. 1H NMR (500 MHz, [CDC13)] 8 : 7.32-7. 19,4. 69,4. 43,4. 29-4.21, 3.16, 2.78, 2.75-2. 70,2. 25-2.15. [13C] NMR (125 MHz, [CDCL3)] [ae] : 174.36, 140.00, 128.64, 128.48, 126.45, 65.59, 53.46, 52.12, 34.03, 31.30, 24.15.

Reference： [1]Patent: WO2003/106445,2003,A1 .Location in patent: Page 32

19
[ 147188-32-7 ]
[ 6305-38-0 ]
N-(5-phenylpentane-1-sulfonyl)-L-homoserine lactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0 - 20℃;	A suspension of preparation 11 (90 mg, 0.39 [MMOL)] in SOCS (286 L, 3.94 [MMOL)] under argon with a catalytic amount of DMF (3 [L,] 0.039 [MMOL)] was heated close to reflux while stirring for [31/2] hrs to yield an oil after the solvent was removed. It was dissolved in DCM (3 mL) and transferred drop-wise via syringe to preparation 1 (65 mg, 0.35 [MMOL)] dissolved by NEt3 [(114] L, 0.82 [MMOL)] in DCM (6 mL). The addition was made at [0C] and under argon and [TOOK 1/2] hour. After 4 hrs of stirring the reaction mixture was allowed to warm to ambient temperature and then left overnight. Quenching [(H20)] the reaction followed by extraction (3x30 mL EtOAc), washing of the combined organic phases with H2O, drying [(MGS04)] and filtration provided a yellow oily crude that was purified by preparative HPLC after removal of solvent in vacuum to provide the title compound. mp=41-43 [C] ; IR (neat): 3253,1778, 1315,1141 [CM-1. 1H] NMR (500 MHz, CDC13) 8 : 7.30-7. 16,4. 97,4. 44,4. 32,4. 28-4.22, 3.17, 2.77-2. 71,2. 64,2. 31-2.23, 1.93-1. 87,1. 90 1.68, 1. [48. 13C] NMR (125 MHz, [CDCL3) a] : 174.61, 142.04, 128.36, 128.32, 125.79, 65.60, 54.34, 52.12, 35.49, 31.14, 30.77, 27.75, 23.43.

Reference： [1]Patent: WO2003/106445,2003,A1 .Location in patent: Page 33

20
[ 14532-24-2 ]
[ 6305-38-0 ]
N-(hexylsulfonyl)-L-homoserine lactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0℃; for 0.5h;	Preparation 1 (199.3mg ; 1. [09MMOL)] was suspended in DCM (5mL), and Et3N (0. [31ML] ; 2. [2MMOL)] was added while stirring. The mixture was cooled to [0C,] and crude preparation 3 (367mg; 1. [99MMOL)] was added. The mixture was stirred for another 30 min. at [0C.] The reaction mixture was evaporated, to dryness and the solid was dissolved in DCM (3mL) and flash chromatographed in the eluent hexan/EtOAc (2: 1) to give the title compound; mp: [47C. 1H] NMR [(CDC13)] [8] : 5.42, 4.42, 4.33, 4.24, 3.17, 2.32, 1.90-1. 70,1. 5-1.2, 0.88. [13C] NMR 8 : 174.9, 65.5, 54.4, 52.0, 31.0, 30.6, 27.7, 23.3, 22.2, 13.8.

Reference： [1]Patent: WO2003/106445,2003,A1 .Location in patent: Page 31

21
[ 927-92-4 ]
[ 6305-38-0 ]
N-(heptylsulfonyl)-L-homoserine lactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0℃; for 0.5h;	Preparation 1 (185. [0MG] ; 1. [02MMOL)] was suspended in DCM (5mL), and Et3N (0. [31ML] ; 2. 2mmol) was added while stirring. The mixture was cooled to [0C,] and preparation5 (290 mg; 1.46 [MMOL)] was added. The mixture was stirred for another 30 min. at [0C.] DCM (5mL) was added and the solution was washed with HCI (3%, [LOML),] [NAHCO3] (5%, [LOML), AND TWICE WITH NACL (SAT. , LOML). THE ORGANIC LAYER WAS DRIED WITH NA2SO4,] evaporated to dryness and the solid was dissolved in DCM (3mL) and flash chromatographed in the eluent hexan-EtOAc (2: 1) to give the title compound; mp: 49- [50C.] [a] [P] [(C] = 10.40mg ; lOmL DCM) [=-14.] [42. 1H] NMR [(CDC13)] 8 : 5.20, 4.45, 4.34, 4.26, 3.18, 2.28, 1.85, 0.88. [13C] NMR 8 : 174.7, 65.5, 54.4, 52.0, 31.4, 30.9, 28.6, 28.1, 23.4, 22.4, 13.9. IR (KBr): 3254,1778, 1314,1139 cm-1. Elemental analysis: Found [(CAL)] : C: 50.27 (50.17) ; H: 8.02 (8.04) ; N: 5.27 (5.32).

Reference： [1]Patent: WO2003/106445,2003,A1 .Location in patent: Page 31

22
[ 10147-36-1 ]
[ 6305-38-0 ]
N-propanesulfonyl-L-homoserine lactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With triethylamine; In dichloromethane; at 0 - 5℃; for 0.5h;	Preparation 1 (192.8mg ; 1. [06MMOL)] was suspended in DCM (5mL), and Et3N (0. [31ML] ; 2. [2MMOL)] was added while stirring. The mixture was cooled to [0C,] and [1-] propanesulfonyl chloride (240.6mg ; 1. [68MMOL)] was added. The mixture was stirred for another 30 min. at 0C. The reaction mixture was evaporated to dryness and the solid was dissolved in DCM (3mL) and flash chromatographed with the eluent hexan/EtOAc (1: 1). to give the title compound. mp: [104-105C.] [a] D (c = 9.28mg ; lOmL DCM) [=-] 28. [02. 1H] NMR [(CI3)] 8 : 6.54, 4.37, 4.25, 4.18, 3.08, 2,58, 2.13, 1. [85. 13C] NMR 8 : 174.9, 65.3, 56.0, 51.6, 30.2, 17.0, 12.6. IR (KBr): 3250,1767, 1352,1144 [CM-1.] Elemental analysis: Found [(CAL)] : C: 40.70 (40.57) ; H: 6.16 (6.32) ; N: 6.66 (6.76);Method 1: General procedure for coupling between a HSL and a sulfonyl chloride :The HSL salt (0.300 [MMOL)] was dissolved in DCM (1-2 mL) and TEA (2.2 equiv) and the mixture was cooled to 5 [C] by means of an ice bath. The sulfonyl chloride (1.1 equiv) was added and the reaction mixture was left with stirring at 5 C for 30 min. The mixture was then evaporated to dryness in vacuum, dissolved in DCM to be purified on the Horizon chromatograph using the solvents EtOAc and hexane. The relevant fractions were combined. Purity was measured by HPLC (215 nm) and the composition was confirmed by HRMS.

Reference： [1]Patent: WO2003/106445,2003,A1 .Location in patent: Page 30, 38-39

23
[ 637031-08-4 ]
[ 6305-38-0 ]
N-(2-oxopropanesulfonyl)-L-homoserine lactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0℃; for 0.5h;	Preparation [1] (100.9mg ; 0. [55MMOL)] was dissolved in DCM (5mL) and Et3N (0.17mL ; [1.] [2MMOL)] was added while stirring. The mixture was cooled to 0 [C] and crude preparation 6 (163mg; 1. [04MMOL)] was added and the reaction mixture was kept at 0 C for another 30 min.. The mixture was evaporated to dryness and the solid was dissolved in DCM (2mL) and flash chromatografed with the eluent EtOAc: hexane (2: 3) to give the title compound; mp: 47C. 1H NMR (DMSO); [No. ]: 8.1-8. 0,4. 6-4.1, 4.41, 2.6-2. 4,2. 25- 1.95, 2. [27. 13C] NMR; 8 : 197.8, 175.3, 65.4, 65.1, 51.7, 30.6, 29.4.

Reference： [1]Patent: WO2003/106445,2003,A1 .Location in patent: Page 32

24
[ 1498463-64-1 ]
[ 6305-38-0 ]
N-(3-benzyloxypropane-1-sulfonyl)-L-homoserine lactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0 - 20℃;	A suspension of preparation 12 (41 mg, 0.16 [MMOL)] in [SOC12] (120 muL, 1.65 [MMOL)] under argon with a catalytic amount of DMF (1 [L,] 0.016 [MMOL)] was heated close to reflux while stirring for [31/2] hrs to yield a yellowish oil after the solvent was removed. It was dissolved in DCM (1 mL) and transferred drop-wise via syringe to preparation 1 (65 mg, 0.35 [MMOL)] dissolved by NEt3 (114 muL, 0.82 [MMOL)] in DCM (2 mL). The addition was made at [0C] and under argon and [TOOK 1/2] hour. After 4 hrs of stirring the reaction mixture was allowed to warm to ambient temperature and then left overnight. Quenching (H2O) the reaction followed by extraction [(3X30] mL EtOAc), washing of the combined organic phases with H2O, drying [(MGS04)] and filtration provided a yellow oily crude product that was purified by preparative HPLC after removal of solvent in vacuum to yield the title [COMPOUND. 1H] NMR (500 MHz, [CDC13)] 8 : 7.36-7. 24,5. 17,4. 49,4. 35, 4.28, 4.21-4. 16,3. 68-3.60, 3.40-3. 28,2. 68-2.63, 2.26-2. 02. [13C] NMR (125 MHz, [CDC13)] 8 : 174.59, 137.85, 128.48, 127.82, 127.71, 73.03, 68.09, 65.60, 52.15, 51.97, 31.05, 24.40.

Reference： [1]Patent: WO2003/106445,2003,A1 .Location in patent: Page 33-34

25
C₁₈H₂₁ClO₂S [ No CAS ]
[ 6305-38-0 ]
N-(6,6-diphenylhexane-1-sulfonyl)-L-homoserine lactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0℃; for 2h;	While stirring a suspension of preparation 13 (46 mg, 0.14 [MMOL)] in [SOC12] (0.1 mL, 1.4 [MMOL)] at RT, a catalytic amount of DMF (1 [PL,] 0.014 [MMOL)] was added. Gas was evolving, as the solid disappeared to form another solid. Heating close to reflux for 2 hrs. Remaining thionyl chloride was removed in reduced pressure (vacuum-pump) overnight leaving a clear, brown oil. It was dissolved in DCM (1 mL) and transferred drop-wise via syringe to preparation 1 (25.5 mg, 0.14 [MMOL)] dissolved by NEt3 (41 muL, 29 [MMOL)] in DCM (3 mL). The addition was made at [0C] and under argon. After 2 hrs of stirring the reaction was quenched by adding water (20 mL). Extraction with EtOAc [(3X30] mL), washing the combined organic phases with [H20,] drying [(MGS04)] and filtration provided a crude product, which was purified by column chromatography to afford the title compound. mp=80-82 [C] ; IR (neat) =3364,1783, 1314,1262, 1098,1025 [CM-1. 1H] NMR (500 MHz, [CDC13)] 8 : 7.29-7. 16,4. 8,4. 43,4. 31-4.21, 3.88, 3.12, 2.76-2. 71,2. 28- 2.19, 2.06, 1.87-1. 79,1. 48,1. [31. 13C] NMR (125 MHz, [CDC13)] 8 : 174.48, 144.95, 128.44, 127.80, 126.12, 65.58, 54.29, 52.13, 51.27, 35.29, 31.27, 28.15, 27.49, 23.43.

Reference： [1]Patent: WO2003/106445,2003,A1 .Location in patent: Page 34

26
[ 1314977-34-8 ]
[ 6305-38-0 ]
N-(6,6-dimethylheptane-1-sulfonyl)-L-homoserine lactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0 - 20℃;	While stirring a suspension of preparation 14 (16 mg, 0.067 [MMOL)] in [SOC12] (50 [PL,] 0.67 [MMOL)] at RT, cat. DMF [(~] [L)] was added. Gas was evolving, as the solid disappeared to form another solid. Heating close to reflux for 3 hrs. Remaining thionyl chloride was removed in reduced pressure (vacuum-pump). The remaining colourless oil was dissolved in DCM (1.5 mL), which over a period of [1/2] hour was inserted drop-wise via syringe to preparation 1 (12 mg, 0.067 [MMOL)] dissolved by NEt3 (41 [L,] 29 [MMOL)] in DCM (3 mL). The addition was made at [0C] and under argon. After 2 hrs of stirring the reaction mixture was allowed to warm to ambient temperature and then left overnight. The solvent was removed at reduced pressure and dissolved in EtOAc (30 mL). Washing (2x20 mL [H20),] drying [(MGS04)] and filtration provided the title compound after removal of solvent in vacuum. mp=81-83 [C] ; IR (neat) =3274,1757, 1330,1138 [CM-1. 1H] NMR (500 MHz, [CDC13)] 8 : 4.71, 4.46, 4.35-4. 24,3. 18,2. 81-2.76, 2.31-2. 22,1. 92-1.85, 1.42, 1.33-1. 26,1. 19-1.16, 0. [89. 13C] NMR (125 MHz, [CDC13)] 8 : 174.43, 665.61, 54.43, 52.17, 43.83, 31.42, 30.27, 29.36, 29.15, 24.09, 23.63.

Reference： [1]Patent: WO2003/106445,2003,A1 .Location in patent: Page 34

27
[ 637031-31-3 ]
[ 6305-38-0 ]
N-(hexylsulfonyl)-L-homoserine lactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With triethylamine; In tert-butyl alcohol; at 30 - 35℃; for 16h;	The HSL salt (0.300 [MMOL)] was dissolved in t-BuOH (1-2 mL) and TEA (2.2 equiv) and a 0.5M solution of OBt-ester in [T-BUOH] (1.0 equiv) was added. The reaction mixture was left with stirring for 16 h at 30-35 [C.] The mixture was then evaporated to dryness in vacuum, dissolved in DCM to be purified on the Horizon chromatograph using the solvents EtOAc and hexane. The relevant fractions were combined. Purity was measured by HPLC (215 nm) and the composition was confirmed by HRMS.

Reference： [1]Patent: WO2003/106445,2003,A1 .Location in patent: Page 39

28
[ 6303-18-0 ]
[ 6305-38-0 ]
N-pentanesulfonyl-L-homoserine lactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0℃; for 0.5h;	Preparation 1 (222. [OMG] ; 1. [22MMOL)] was suspended in DCM (5mL), and Et3N (0.34mL ; 2. [4MMOL)] was added while stirring. The mixture was cooled to [0C,] and preparation 2 (191. Omg; 1. [12MMOL)] was added. The mixture was stirred for another 30 min. at [0C.] DCM [(5ML)] was added and the solution was washed with HCI (3%, [LOML),] [NAHCO3] (5%, [LOML), AND TWICE WITH NACL (SAT. , LOML). THE ORGANIC LAYER WAS DRIED WITH NA2SO4,] evaporated to dryness and the solid was dissolved in DCM (3mL) and flash chromatographed in the eluent hexan-EtOAc (3: 2) to give the title compound; mp: 47- [49C.] [a] [P] [(C] = 11.03mg ; lOmL [DCM) =-14. 51. 1H] NMR [(CI3)] [S] : 5.41, 4.43, 4.33, 4.24, 3.36, 2.70, 2.28, 1.95-1. 70,1. 50-1.20, 0. [88. 13 C] NMR 8 : 174.9, 65.5, 54.3, 52.0, 30.6, 30.1, 23.0, 22.0, 13.6. IR (KBr): 3264,1778, 1326,1140 [CM-1.] Elemental analysis : Found [(CAL)] : C: 45.96 (45.93) ; H: 7.20 (7.28) ; N: 5.82 (5.98).

Reference： [1]Patent: WO2003/106445,2003,A1 .Location in patent: Page 30-31

29
[ 40542-90-3 ]
[ 6305-38-0 ]
C₁₇H₂₁NO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48.3%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In pyridine; dichloromethane; at 0℃; for 18h;	Under a N2 atmosphere, <strong>[6305-38-0]L-homoserine lactone hydrobromide</strong> (10 g, 55 mmol), mono-benzyladipate (2), pyridine (50 mL) and EDC hydrochloride (11.5 g, 60 mmol) were combined in dichloromethane (100 mL) in a 500 mL round-bottomed flask with cooling (0 C.). The resulting mixture was stirred for 18 hours. The mixture was cooled to 0 C. and ice cold 15% citric acid solution was added. The citric acid layer was separated and extracted with dichloromethane (1100 mL). The extract was combined with the remaining dichloromethane reaction solution and the combined dichloromethane solutions were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuum, yielding 17.4 g (98.8%) of the crude product, which was slurried in isopropyl acetate to produce an off-white solid. The solid was collected and dried under high vacuum at 30 C., to produce 8.5 g (48.3%) of the desired product.

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 9850 - 9861
[2]Patent: US6703513,2004,B1 .Location in patent: Page column 43

30
[ 2018-66-8 ]
[ 6305-38-0 ]
[ 167766-55-4 ]

Yield	Reaction Conditions	Operation in experiment
68%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 15h;	1.1) N2-[(benzyloxy)carbonyl]-N1-[(3S)-2-oxotetrahydrofuran-3-yl]-L-leucinamide: 3.51 g (13.25 mmol) of Cbz-L-Leucine, 2.41 g (1 eq.) of (S)-2-amino-4-butyrolactone hydrobromide, 1.97 g of HOBT (1.1 eq.) and 5.59 g (2.2 eq.) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) is dissolved in 60 ml of anhydrous DMF then 7.64 ml (3.3 eq.) of N,N-diisopropylethylamine is added. The reaction mixture is stirred for 15 hours at 20 C. before being poured into 200 ml of a 1/1 mixture of ethyl acetate/water. After stirring and decantation, the organic solution is washed successively with 100 ml of a saturated solution of NaHCO3, 50 ml of water, 100 ml of a 1M solution of citric acid and finally 100 ml of a solution of salt water. The organic phase is dried over sodium sulphate, filtered and concentrated to dryness under vacuum. The oil obtained is washed using isopentane and then crystallized from a dichloromethane/isopentane mixture. A white solid is obtained with a yield of 68%. Melting point: 130-131 C.
68%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 15h;	1.1) N2-[(benzyloxy)carbonyl]-N'-[(3S-2-oxotetrahydrofuran-3-yl]-L-leucinamide 3.51 g (13.25 mmol) of Cbz-L-Leucine, 2.41 g (1 eq.) of (S)-2-amino-4-butyrolactone hydrobromide, 1.97 g of HOBT (1.1 eq.) and 5.59 g (2.2 eq.) of -1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (EDC) are dissolved in 60 ml of anhydrous DMF, then 7.64 ml of (3.3 eq.) of N,N-diisopropylethylamine is added. The reaction mixture is stirred for 15 hours at 20 C. before of being poured into 200 ml of a 1/1 mixture of ethyl acetate/water. After stirring and decantation, the organic solution is washed successively with 100 ml of a saturated solution of NaHCO3, 50 ml of water, 100 ml of a 1M solution of citric acid and finally 100 ml of a solution of salt water. The organic phase is dried over sodium sulphate, filtered and concentrated to dryness under vacuum. The oil obtained is washed using isopentane and then crystallized from a dichloromethane/isopentane mixture. A white solid is obtained with a yield of 68%. Melting point: 130-131 C.

Reference： [1]Patent: US2005/222045,2005,A1 .Location in patent: Page/Page column 10
[2]Patent: US2009/18120,2009,A1 .Location in patent: Page/Page column 6

31
[ 10488-94-5 ]
[ 6305-38-0 ]
[ 318489-23-5 ]

Yield	Reaction Conditions	Operation in experiment
47%		N-(alpha-Methyl-b-ketooctanoyl)-(S)-homoserine: The reaction was carried out with ethyl 2-methyl-3-oxooctanoate (0.57 mmol) and (S)-homoserine lactone hydrobromide (0.85 mmol). Purification was carried out by radial silica gel column chromatography (EtOAc:CH2Cl2, 1:4, then iPrOH:CH2Cl2, 1:20) to afford the product as a white solid (69 mg, 47%). 1H NMR (400 MHz, CDCl3) d 6.95 (bs, 1H), 4.57-4.44 (m, 2H), 4.30-4.22 (m, 1H), 3.50-3.42 (m, 1H), 2.81-2.70 (m, 1H), 2.58-2.52 (m, 2H), 2.25-2.10 (m, 1H), 1.60-1.52 (m, 2H), 1.45-1.38 (m, 3H), 1.25-1.19 (m, 4H), 0.87 (t, J=7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3) d 210.56, 210.52, 175.73, 175.72, 171.42, 171.39, 66.91, 66.86, 54.59, 54.55, 50.26, 50.19, 42.79, 42.54, 32.2, 30.9, 24.0, 23.4, 16.33, 16.25, 14.9; HRMS Calcd for M+H C13H21NO4: 256.1549. Found: 256.1560.

Reference： [1]Patent: US6518066,2003,B1

32
[ 318489-24-6 ]
[ 6305-38-0 ]
[ 318489-25-7 ]

Yield	Reaction Conditions	Operation in experiment
41%		N-(alpha,alpha-Dimethyl-b-ketooctanoyl)-(S)-homoserine: After ester hydrolysis the reaction was carried out with 2,2-dimethyl-3-oxooctanoic acid (0.46 mmol) and (S)-homoserine lactone hydrobromide (0.85 mmol). Purification was carried out by radial silica gel column chromatography (EtOAc:CH2Cl2, 1:4, then CH2Cl2:EtOAc:hexane, 1:1:3) to afford the product as a white solid (51 mg, 41%). 1H NMR (400 MHz, CDCl3) d 6.45 (bs, 1H), 4.53-4.43 (m, 2H), 4.32-4.23 (m, 1H), 2.81-2.72 (m, 1H), 2.52 (t, J=7.2 Hz, 2H), 2.21-2.09 (m, 1H), 1.60-1.51 (m, 2H), 1.41 (d, J=2.4 Hz, 6H), 1.30-1.19 (m, 4H), 0.87 (t, J=7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3) d 211.1, 174.9, 173.2, 66.0, 55.7,49.5, 38.3, 31.4, 29.9, 23.5, 22.7, 22.6, 14.0; HRMS Calcd for M+H C14H23NO4: 270.1705. Found: 270.1700.

Reference： [1]Patent: US6518066,2003,B1

33
[ 318489-31-5 ]
[ 6305-38-0 ]
[ 318489-26-8 ]

Yield	Reaction Conditions	Operation in experiment
74%		N-(alpha-Ethyl-b-ketooctanoyl)-(S)-homoserine: After ester hydrolysis the reaction was carried out with 2-ethyl-3-oxooctanoic acid (0.81 mmol) and (S)-homoserine lactone hydrobromide (0.77 mmol). Purification was carried out by radial silica gel column chromatography (EtOAc:CH2Cl2, 1:4, then EtOAc:hexane, 1:1) to afford the product as a white solid (155 mg, 74%). 1H NMR (400 MHz, CDCl3) d 6.97 (bd, J=35.5 Hz, 1H), 4.58-4.50 (m, 1H), 4.50-4.42 (m, 1H), 4.30-4.21 (m, 1H), 3.37 (q, J=8.0 Hz, 1H), 2.81-2.68 (m, 1H), 2.58-2.50 (m, 2H), 2.23-2.10 (m, 1H), 1.98-1.80 (m, 2H), 1.62-1.52 (m, 4H), 1.36-1.20 (m, 4H), 0.96 (q, J=5.6 Hz, 3H), 0.87 (t, J=7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3) d 209.90, 209.83, 174.7, 169.6, 169.5, 66.0, 65.9, 61.3, 61.2, 49.3, 49.2, 43.2, 42.9, 31.3, 30.05, 30.01, 24.96, 24.94, 23.0, 22.5, 14.0, 11.93, 11.90; HRMS Calcd for M+H C14H23NO4: 270.1705. Found: 270.1692.

Reference： [1]Patent: US6518066,2003,B1

34
[ 318489-27-9 ]
[ 6305-38-0 ]
[ 318489-28-0 ]

Yield	Reaction Conditions	Operation in experiment
		N-(alpha-Butyl-b-ketooctanoyl)-(S)-homoserine: After ester hydrolysis the reaction was carried out with 2-butyl-3-oxooctanoic acid (0.23 mmol) and (S)-homoserine lactone hydrobromide (0.36 mmol). Purification was carried out by radial silica gel column chromatography (EtOAc:hexane, 1:1, then EtOAc:CH2Cl2, 1:4) to afford. the product as a white solid (36 mg, 52%). 1H NMR (400 MHz, CDCl3) d 6.89 (bd, J=35.5 Hz, 1H), 4.56-4.41 (m, 2H), 4.33-4.21 (m, 1H), 3.42 (q, J=7.4 Hz, 1H), 2.80-2.70 (m, 1H), 2.56-2.48 (m, 2H), 2.22-2.08 (m, 1H), 1.96-1.72 (m, 2H), 1.63-1.50 (m, 2H), 1.38-1.20 (m, 8H), 0.93-0.84 (m, 6H); 13C NMR (100 MHz, CDCl3) d 207.2, 207.1, 174.8, 169.69, 169.62, 66.0, 65.9, 60.82, 60.80, 49.4, 49.3, 31.6, 30.85, 30.83, 29.9, 29.8, 29.6, 29.14, 29.13, 27.38, 27.36, 22.6, 14.1; HRMS Calcd for M+H C16H27NO4: 298.2018. Found: 298.2020.

Reference： [1]Patent: US6518066,2003,B1

35
[ 5633-90-9 ]
[ 6305-38-0 ]
N-(α-Hexyl-b-ketobutanoyl)-(S)-homoserine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%		N-(alpha-Hexyl-b-ketobutanoyl)-(S)-homoserine: After ester hydrolysis the reaction was carried out with 2-hexyl-3-oxobutanoic acid (0.83 mmol) and (S)-homoserine lactone hydrobromide (0.65 mmol). Purification was carried out by radial silica gel column chromatography (EtOAc:hexane, 1:1, then EtOAc:CH2Cl2, 1:3) to afford the product as a white solid (147 mg, 84%). 1H NMR (400 MHz, CDCl3) d 6.87 (bd, J=21.3 Hz, 1H), 4.58-4.43, (m, 2H), 4.30-4.22 (m, 1H), 3.40 (q, J=8.0 Hz, 1H), 2.80-2.70 (m, 1H), 2.25 (d, J=2.4 Hz, 3H), 2.23-2.12 (m, 1H), 1.91-1.78 (m, 2H), 1.35-1.20 (m, 6H), 0.92-0.82 (m, 3H), 0.85 (t, J=6.8 Hz, 3H); 13C NMR (100 MHz, CDCl3) d 209.8, 174.7, 169.7, 169.6, 66.0, 65.9, 65.32, 65.30, 65.2, 60.0,49.3, 49.2, 43.2, 42.9, 31.35, 31.33, 31.27, 31.24, 30.0, 29.6, 29.5, 23.1, 22.5, 14.0, 13.9.

Reference： [1]Patent: US6518066,2003,B1

36
[ 10051-44-2 ]
[ 6305-38-0 ]
N-hexanoyl-L-homoserine lactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40.3%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile;	N-hexanoyl (L-)-homoserine lactone were provided as follows. To O.583g (3 mmoles) of sodium caproate and 0.546g (3 mmoles) of (S)-(-)-alpha-amino-gamma- butyrolactone hydrobromide in 25 mL dry acetonitrile (CH3CN) were added 0.604g (3.15mmoles) of l-[3-(dimethylamino)pro?yl]-3-ethylcarbodiimide hydrochloride. After stirring overnight, the CH3CN was evaporated and the residue transferred to a separatory funnel with 100 mL of ethyl acetate (EtOAc). The EtOAc layer was washed with 50 mL of 10% ammonium chloride (NH4Cl). The aqueous layer was extracted with 100 mL more of EtOAc and combined and dried (Na2SO4). The residue, after evaporation of the EtOAc, was chromatographed on a 2x39 cm column of silica gel eluting first with methylene chloride (CH2Cl2; 150 mL), then (4 acetone/20 CH3CN/ 76 CH2Cl2) until the compound eluted. The combined fractions were evaporated, taken up in CH2Cl2, filtered, and concentrated to a minimum volume upon which a gel-like solid formed. The solid was collected and washed with petroleum ether and dried. TLC indicated one spot with Rf of 0.55 in (4 acetone/20 CH3CN/76 EtOAc) using a lactone spray. The yield from four crops was 0.516g or 40.3%.

Reference： [1]Patent: WO2006/110531,2006,A2 .Location in patent: Page/Page column 9-10

37
[ 6305-38-0 ]
[ 98-59-9 ]
[ 10396-97-1 ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 7379 - 7383
[2]Journal of Organic Chemistry,2011,vol. 76,p. 201 - 215
[3]Journal of Organic Chemistry,2008,vol. 73,p. 7028 - 7036
[4]Organic and Biomolecular Chemistry,2007,vol. 5,p. 3510 - 3519

38
[ 74-93-1 ]
[ 6305-38-0 ]
[ 63-68-3 ]

Yield	Reaction Conditions	Operation in experiment
33%	With aluminum tri-bromide; at 20 - 40℃; for 3h;Product distribution / selectivity;	In a high-pressure autoclave, aluminium bromide (75 mmol) was carefully added to MeSH (50 ml). Subsequently, the bromide salt of the aminolactone (obtained from Aldrich) (25 mmol) was added. The autoclave was shaken for 1 hour at room temperature and thereafter for 2 hours at 40 C. The autoclave was cooled and expanded. After removal of the MeSH, the residue was quenched with water and the pH made basic using NaOH. The resultant precipitate was removed by filtration. The methionine yield was 33%.

Reference： [1]Patent: US7368600,2008,B2 .Location in patent: Page/Page column 17

39
C₁₀H₁₈F₂O₂ [ No CAS ]
[ 6305-38-0 ]
N-(2,2-difluorodecanoyl)-L-homoserine lactone [ No CAS ]

Reference： [1]Patent: US6337347,2002,B1 .Location in patent: Page column 9

40
C₁₂H₂₀F₂O₃ [ No CAS ]
[ 6305-38-0 ]
C₁₆H₂₅F₂NO₄ [ No CAS ]

Reference： [1]Patent: US6337347,2002,B1 .Location in patent: Page column 9

41
[ 6305-38-0 ]
[ 502497-41-8 ]
C₁₆H₂₇F₂NO₃ [ No CAS ]

Reference： [1]Patent: US6337347,2002,B1 .Location in patent: Page column 9

42
[ 252726-17-3 ]
[ 6305-38-0 ]
[ 218150-36-8 ]

Reference： [1]Patent: US6337347,2002,B1 .Location in patent: Page column 9

43
[ 252726-20-8 ]
[ 6305-38-0 ]
C₁₆H₂₇F₂NO₃ [ No CAS ]

Reference： [1]Patent: US6337347,2002,B1 .Location in patent: Page column 9

44
[ 41167-78-6 ]
[ 6305-38-0 ]
[ 252726-06-0 ]

Reference： [1]Patent: US6337347,2002,B1 .Location in patent: Page column 9

45
[ 252726-21-9 ]
[ 6305-38-0 ]
(S)-2-(nonylsulfonyl)-N-(2-oxotetrahydrofuran-3-yl)acetamide [ No CAS ]

Reference： [1]Patent: US6337347,2002,B1 .Location in patent: Page column 9

46
2-(N-octylsulfamoyl)acetic acid [ No CAS ]
[ 6305-38-0 ]
(S)-2-(N-octylsulfamoyl)-N-(2-oxotetrahydrofuran-3-yl)acetamide [ No CAS ]

Reference： [1]Patent: US6337347,2002,B1 .Location in patent: Page column 9

47
[ 380228-21-7 ]
[ 6305-38-0 ]
C₂₅H₃₅NO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%		A 250 mL three-necked round-bottomed flask was charged with compound 11 (5.47 g, 15.1 mmol) to which dichloromethane (50 mL) and 3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.04 g, 15.8 mmol) were added under a N2 atmosphere. The resulting dark amber solution was stirred at room temperature for 2.5 hours. Homoserine lactone hydrobromide (2.75 g, 15.1 mmol) was mixed with Hunig's Base (2.63 mL) and dichloromethane (55 mL) and added to the reaction solution via an addition funnel and stirred overnight. TLC (1:19 sodium acid/dichloromethane, 2 drops of acetic acid) of the resulting product after 18 hours showed the starting materials had been consumed. [00369] The solution was poured into a mixture of ice water (150 ml) and 2N hydrochloric acid (11 mL). Saturated, aqueous sodium chloride (50 mL), hexanes (50 mL) and dichloromethane (50 mL) were added to separate the layers and the aqueous phase was drawn off with dichloromethane (2110 mL). The organic phase was washed with a saturated, aqueous sodium chloride/water mixture (1:1,320 mL). The product solution was dried with sodium sulfate, filtered slowly through a silica pad (232 g), eluted with 90% ethyl acetal/hexanes (500 mL) and the solvents were removed under vacuum at 41 C. and the white, solid product was weighed to 4.28 g (64% yield).

Reference： [1]Patent: US6703513,2004,B1 .Location in patent: Page column 46

48
[ 111-14-8 ]
[ 6305-38-0 ]
N-(β-ketocaproyl)-L-homoserine lactone [ No CAS ]

Reference： [1]Journal of Natural Products,2008,vol. 71,p. 1032 - 1036

49
[ 6305-38-0 ]
[ 254907-27-2 ]
N-(3-oxooctanoyl)-L-homoserine lactone [ No CAS ]

Reference： [1]Journal of Natural Products,2008,vol. 71,p. 1032 - 1036
[2]Journal of the Brazilian Chemical Society,2011,vol. 22,p. 702 - 708

50
[ 6305-38-0 ]
[ 111861-21-3 ]
[ 177158-19-9 ]

Reference： [1]Journal of Natural Products,2008,vol. 71,p. 1032 - 1036

51
[ 6305-38-0 ]
[ 182359-65-5 ]
[ 168982-69-2 ]

Reference： [1]Journal of Natural Products,2008,vol. 71,p. 1032 - 1036

52
C₂₂H₃₆N₃O₈S^(1-)*Li⁽¹⁺⁾ [ No CAS ]
[ 6305-38-0 ]
[ 1083287-18-6 ]

Reference： [1]Synlett,2008,p. 2122 - 2126

53
[ 1025737-52-3 ]
[ 6305-38-0 ]
[ 172617-17-3 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 2047 - 2050

54
[ 1025737-66-9 ]
[ 6305-38-0 ]
[ 1025737-37-4 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 2047 - 2050

55
[ 6305-38-0 ]
[ 530-62-1 ]
[ 1108657-76-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 20℃; for 3h;	Step 1: Preparation of (5)-/V-(2-oxotetrahydrofuran-3-yl)-lH-imidazole-l- carboxamide 42. To a stirred solution of CDI (14.7 g, 1.1 eq.), TEA (12.6 mL, 1.1 eq.) in DCM (160 mL) was added (5)-(-)-alpha-amino-gamma-butyrolactone hydrobromide (15 g, 1 eq.) under nitrogen. The reaction mixture was stirred at room temperature for 3 hrs. The reaction mixture was concentrated and used directly in the next step without further purification.

Reference： [1]Patent: WO2009/14730,2009,A1 .Location in patent: Page/Page column 103

56
[ 2018-66-8 ]
salt water [ No CAS ]
3-dimethylaminopropylcarbodiimide monohydrochloride [ No CAS ]
[ 6305-38-0 ]
[ 167766-55-4 ]

Yield	Reaction Conditions	Operation in experiment
68%	With sodium hydrogencarbonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; citric acid; In methylbutane; water; ethyl acetate; N,N-dimethyl-formamide;	1.1) N2-[(benzyloxy)carbonyl)-N1-[(3S)-2-oxotetrahydrofuran-3-yl]-L-leucinamide 3.51 g (13.25 mmol) of Cbz-L-Leucine, 2.41 g (1 eq.) of (S)-2-amino-4-butyrolactone hydrobromide, 1.97 g of HOBT (1.1 eq.) and 5.59 g (2.2 eq.) of 1-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) are dissolved in 60 ml of anhydrous DMF, then 7.64 ml of (3.3 eq.) of N,N-diisopropylethylamine is added. The reaction mixture is stirred for 15 hours at 20 C. before being poured into 200 ml of a 1/1 mixture of ethyl acetate/water. After stirring and decantation, the organic solution is washed successively with 100 ml of a saturated solution of NaHCO3, 50 ml of water, 100 ml of a 1M solution of citric acid and finally 100 ml of a solution of salt water. The organic phase is dried over sodium sulphate, filtered and concentrated to dryness under vacuum. The oil obtained is washed using isopentane and then crystallized from a dichloromethane/isopentane mixture. A white solid is obtained with a yield of 68%. Melting point: 130-131 C.

Reference： [1]Patent: US2009/149430,2009,A1

57
C₁₅H₂₃N₃O₅ [ No CAS ]
[ 6305-38-0 ]
[ 1175052-11-5 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 10610 - 10619

58
C₁₆H₂₅N₃O₅ [ No CAS ]
[ 6305-38-0 ]
[ 1175052-13-7 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 10610 - 10619

59
C₁₇H₂₇N₃O₅ [ No CAS ]
[ 6305-38-0 ]
[ 1175052-15-9 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 10610 - 10619

60
C₂₀H₃₃NO₇ [ No CAS ]
[ 6305-38-0 ]
[ 1175052-28-4 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 10610 - 10619

61
[ 1334318-42-1 ]
[ 6305-38-0 ]
[ 1175052-30-8 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 10610 - 10619

62
C₂₂H₃₇NO₇ [ No CAS ]
[ 6305-38-0 ]
[ 1175052-32-0 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 10610 - 10619

63
[ 133-32-4 ]
[ 6305-38-0 ]
N-(indole-3-butanoyl)-L-homoserine lactone [ No CAS ]

Reference： [1]Chemical Communications,2009,p. 2836 - 2838

64
[ 6305-38-0 ]
[ 1878-68-8 ]
(S)-2-(4-bromophenyl)-N-(2-oxotetrahydrofuran-3-yl)acetamide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 8452 - 8464
[2]Chemical Communications,2009,p. 2836 - 2838

65
[ 6305-38-0 ]
[ 101-54-2 ]
[ 339007-87-3 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of 1.48 g (8.15 mmoles) of (S)-2-amino-4-butyrolactone hydrobromide and 3.12 ml (17.9 mmoles) of diisopropylethylamine in 80 ml of anhydrous CH2Cl2 is added slowly (4 hours) into a three-necked flask containing a solution of 0.89 g (3 mmoles) of triphosgene in 45 ml of anhydrous CH2Cl2, under an inert atmosphere. After stirring for a further 15 minutes, a solution of 1.5 g (8.15 mmoles) of N1-phenyl-1,2-benzenediamine and 3.12 ml (17.9 mmoles) of diisopropylethylamine in 45 ml of anhydrous CH2Cl2 is added in one go. The reaction mixture is then heated for 5 hours at 60 C. After concentration to dryness under vacuum, the residue is divided between 50 ml of AcOEt and 50 ml of water. After stirring and decanting, the organic phase is washed successively with 50 ml of water and 50 ml of salt water. The organic solution is then dried over Na2SO4, filtered and concentrated under vacuum. The evaporation residue is then purified on a silica column (eluent: Heptane/AcOEt: 1/2). Pink solid. [00398] Melting point: 63-65 C.

Reference： [1]Patent: US6747024,2004,B1 .Location in patent: Page column 36-37

66
[ 103-82-2 ]
[ 6305-38-0 ]
(S)-N-(2-oxo-tetrahydrofuran-3-yl)-2-phenylacetamide [ No CAS ]