[ CAS No. 504-78-9 ] {[proInfo.proName]}

Name: 504-78-9|Thiazolidine|98%
Brand: Ambeed
SKU: A475228
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Quality Control of [ 504-78-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 504-78-9 ]

CAS No. :	504-78-9	MDL No. :	MFCD00005211
Formula :	C₃H₇NS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OGYGFUAIIOPWQD-UHFFFAOYSA-N
M.W :	89.16	Pubchem ID :	10444
Synonyms :

Calculated chemistry of [ 504-78-9 ]

Physicochemical Properties

Num. heavy atoms :	5
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	28.73
TPSA :	37.33 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.22
Log Po/w (XLOGP3) :	0.32
Log Po/w (WLOGP) :	-0.1
Log Po/w (MLOGP) :	-0.1
Log Po/w (SILICOS-IT) :	1.66
Consensus Log Po/w :	0.6

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.59
Solubility :	22.7 mg/ml ; 0.254 mol/l
Class :	Very soluble
Log S (Ali) :	-0.67
Solubility :	19.2 mg/ml ; 0.215 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.77
Solubility :	15.0 mg/ml ; 0.169 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.9

Safety of [ 504-78-9 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P403+P235	UN#:	1993
Hazard Statements:	H225	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 504-78-9 ]

* 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 [ 504-78-9 ]
Downstream synthetic route of [ 504-78-9 ]

[ 504-78-9 ] Synthesis Path-Upstream 1~2

1
[ 504-78-9 ]
[ 24424-99-5 ]
[ 148312-55-4 ]

Reference： [1] Tetrahedron Asymmetry, 2004, vol. 15, # 19, p. 3059 - 3072
[2] Chemical Communications, 2018, vol. 54, # 11, p. 1303 - 1306
[3] Nucleosides and Nucleotides, 1996, vol. 15, # 5, p. 1113 - 1120
[4] Patent: US5258513, 1993, A,

2
[ 504-78-9 ]
[ 84348-37-8 ]
[ 401564-36-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at 2 - 7℃; for 2 h; Large scale	To (2S)-1-tert-butoxycarbonyl-4-oxopyrrolidine-2-carboxylic acid (Compound 8a) (60.0 kg),thiazolidine (30.3 kg) and N,N-diisopropylethylamine ( 118kg) in ethyl acetate and propylphosphonic anhydride (595kg) (cyclic trimer) was added 28wpercent at 2 -7 °C in ethyl acetate (446kg) was added and the reaction mixture was 2 -4 °C stirred for 2 hours. To this reaction mixture was added 15wpercent aqueous citric acid (600kg) for distribution, and the aqueous layer with ethyl acetate (271kg) extract. The ethyl acetate layer obtained was mixed, and sequentially washed with 10wpercent aqueous solution of diammoniumphosphate (600kg) and water (300kg). The ethyl acetate layer was concentrated to a residual volume 300L, n-heptane (739kg) at 23 -25 °C added, and the mixture wasstirred at 23 -25 °C 1 hour and stirred at 1 -5 °C. The precipitated crystals were collected by filtration, with n-heptane (164 kg) were washed and driedunder reduced pressure to yield 3-[(2S)-1-tert-butoxycarbonyl-4-oxopyrrolidin-2-ylcarbonyl]thiazolidine (compound 9a) (67.8 kg, yield 86 percent)
81.7%	Stage #1: With dicyclohexyl-carbodiimide In toluene at -10 - -5℃; Stage #2: With dmap In toluene at -6 - 5℃; for 1.33333 h;	A solution of DCC (107.8 g) in toluene (300 mL) was added to a solution of 1-(tert-butoxycarbonyl)-4-oxo-L-proline (prepared according to the process of Example 2; 100 g) in toluene (900 mL) at -5°C to - 10°C, and the reaction mixture was stirred for 30 minutes at the same temperature. Dimethylaminopyridine (1 g) and thiazolidine (46.7 g) were slowly added to the reaction mixture at a temperature of about -6°C to -2°C over a period of about 15 to 20 minutes. The reaction mixture was allowed to warm to a temperature of 0°C to 5°C, and stirred at the same temperature for 60 minutes. When the reaction was complete, the reaction mixture was quenched with deionized water (20 mL), and stirred at 20°C to 25°C for 30 minutes. The resulting mixture was filtered through a Hyflo® bed. The filtrate was washed with aqueous sodium bicarbonate solution (50 g sodium carbonate in 500 mL deionized water). The organic layer was separated and washed with an aqueous solution of sodium chloride (50 g sodium chloride in 500 mL deionized water). Activated carbon (10 g) was added to the organic layer, and the reaction mixture was stirred at 25°C to 30°C for 30 minutes. The reaction mixture was filtered through a Hyflo® bed, and concentrated at a temperature of 50°C under reduced pressure. The residue obtained was dissolved in ethyl acetate (200 mL) at 50°C to 55°C. Hexanes (800 mL) were added at 50°C to 55°C over a period of 1 to 2 hours. The reaction mixture was further cooled to a temperature of 0°C to 5°C, and stirred at the same temperature for 3 hours. The reaction mixture was filtered to obtain a solid. The solid was washed with a pre-cooled (0°C to 5°C) mixture of ethyl acetate (80 mL) and hexanes (320 mL), and dried at a temperature of 40°C to 45°C under reduced pressure to obtain tert-Butyl (2S)-4-oxo-2-(1.3-thiazolidin-3- ylcarbonyl)pyrrolidine-1-carboxylate. Yield: 81.7percent
81.7%	With dmap; dicyclohexyl-carbodiimide In toluene at -6 - 5℃; for 1.33333 h;	A solution of DCC (107.8 g) in toluene (300 mL) was added to a solution of 1- (tert-butoxycarbonyl)-4-oxo-L-proline (Formula V, prepared according to Example 2; 100 g) in toluene (900 mL) at -10°C to -5°C. The reaction mixture was stirred for 30 minutesat -10°C to -5°C. 4-Dimethylaminopyridine (1 g) and thiazolidine (46.7 g) were slowly added to the reaction mixture at -6°C to -2°C over a period of 15 minutes to 20 minutes. The reaction mixture was allowed to warm to 0°C to 5°C, then stirred at the same temperature for 60 minutes. When the reaction was complete, the reaction mixture was quenched with deionized water (20 mL), then stirred at 20°C to 25°C for 30 minutes. Theresulting mixture was filtered through a Hyflo® bed. The filtrate was washed with an aqueous sodium bicarbonate solution (50 g sodium carbonate in 500 mL deionized water). The organic layer was separated, then washed with an aqueous solution of sodium chloride (50 g sodium chloride in 500 mL deionized water). Activated carbon (10 g) was added to the organic layer, then the reaction mixture was stirred at 25°C to 30°C for 30 minutes.The reaction mixture was filtered through a Hyflo® bed, then concentrated at 50°C under reduced pressure. The residue obtained was dissolved in ethyl acetate (200 mL) at 50°C to 55°C. Hexanes (800 mL) were added at 50°C to 55°C over a period of one hour to 2 hours. The reaction mixture was further cooled to 0°C to 5°C, then stirred at the same temperature for 3 hours. The reaction mixture was filtered to obtain a solid. The solidwas washed with a precooled (0°C to 5°C) mixture of ethyl acetate (80 mL) and hexanes (320 mL), then dried at 40°C to 45°C under reduced pressure to obtain tert-butyl (2S)-4- oxo-2-( 1,3 -thiazolidin-3 -ylcarbonyl)pyrrolidine- 1 -carboxylate.Yield: 81.7percent HPLC Purity: 98.97 percent

Reference： [1] Patent: CN103649055, 2016, B, . Location in patent: Paragraph 0144-0147
[2] Patent: WO2015/19238, 2015, A1, . Location in patent: Page/Page column 9; 10
[3] Patent: WO2016/79699, 2016, A1, . Location in patent: Page/Page column 12

[ 504-78-9 ] Synthesis Path-Downstream 1~41

1
[ 504-78-9 ]
[ 68077-26-9 ]
7-<(2-aminoethyl)thio>-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 394 - 404

2
[ 504-78-9 ]
[ 4463-59-6 ]
[ 99507-82-1 ]

Reference： [1]European Journal of Medicinal Chemistry,1985,vol. 20,p. 309 - 313

3
[ 504-78-9 ]
C₁₅H₂₅NO₅ [ No CAS ]
[ 155251-72-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In chloroform for 3h; Ambient temperature; Yield given;

Reference： [1]Arai; Nishioka; Niwa; Yamanaka; Tanaka; Yoshinaga; Kobayashi; Miura; Ikeda [Chemical and Pharmaceutical Bulletin, 1993, vol. 41, # 9, p. 1583 - 1588]

4
[ 504-78-9 ]
[ 24424-99-5 ]
[ 148312-55-4 ]

Yield	Reaction Conditions	Operation in experiment
86.2%	In 1,4-dioxane; water;	a. N-tert-butoxycarbonyl-thiazolidine. 24 g (0.11 mole) of di-tert-butyl dicarbonate dissolved in 50 ml of dioxane are added dropwise to a solution of 8.9 g (0.1 mole) of thiazolidine in 50 ml of dioxane and 50 ml of water, while maintaining the pH between 10 and 10.5 by addition of soda lye. The mixture is stirred at room temperature for 6 hours. The formed salts are filtered off and the organic solvent is evaporated under reduced pressure. The aqueous residue is extracted with dichloromethane (2*50 ml), the organic phase is decanted, dried over sodium sulfate and the solvent is evaporated off. The residue is purified by distillation under reduced pressure. 16.3 g of N-tert-butoxycarbonyl-thiazolidine are obtained. Yield: 86.2%. B.P.: 56-57 C./6.7 mbars.

Reference： [1]Tetrahedron Asymmetry,2004,vol. 15,p. 3059 - 3072
[2]Chemical Communications,2018,vol. 54,p. 1303 - 1306
[3]Nucleosides and Nucleotides,1996,vol. 15,p. 1113 - 1120
[4]Patent: US5258513,1993,A

5
[ 504-78-9 ]
[ 29684-56-8 ]
C₅H₁₀N₂O₄S₂ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2002,vol. 41,p. 3866 - 3870
[2]Patent: US2004/138448,2004,A1 .Location in patent: Figure 5

6
[ 504-78-9 ]
[ 57133-29-6 ]
(4-tert-butoxycarbonylamino-5-oxo-5-thiazolidin-3-yl-pentyl)-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 5005 - 5014

7
[ 504-78-9 ]
[ 331763-66-7 ]
[1-(3-fluoro-benzyl)-3-oxo-3-thiazolidin-3-yl-propyl]-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide

Reference： [1]Xu, Jinyou; Ok, Hyun O.; Gonzalez, Edward J.; Colwell Jr., Lawrence F.; Habulihaz, Bahanu; He, Huaibing; Leiting, Barbara; Lyons, Kathryn A.; Marsilio, Frank; Patel, Reshma A.; Wu, Joseph K.; Thornberry, Nancy A.; Weber, Ann E.; Parmee, Emma R. [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 18, p. 4759 - 4762]

8
[ 504-78-9 ]
[ 218609-00-8 ]
[1-(4-fluoro-benzyl)-3-oxo-3-thiazolidin-3-yl-propyl]-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4759 - 4762

9
[ 504-78-9 ]
[ 269398-80-3 ]
[1-(2-methyl-benzyl)-3-oxo-3-thiazolidin-3-yl-propyl]-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide

10
[ 504-78-9 ]
[ 218608-96-9 ]
[1-(4-chloro-benzyl)-3-oxo-3-thiazolidin-3-yl-propyl]-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4759 - 4762

11
[ 504-78-9 ]
[ 269726-86-5 ]
[1-(4-cyano-benzyl)-3-oxo-3-thiazolidin-3-yl-propyl]-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide

12
[ 504-78-9 ]
[ 269726-80-9 ]
[1-(2-cyano-benzyl)-3-oxo-3-thiazolidin-3-yl-propyl]-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide

13
[ 504-78-9 ]
[ 269726-83-2 ]
[1-(3-cyano-benzyl)-3-oxo-3-thiazolidin-3-yl-propyl]-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide

14
[ 504-78-9 ]
[ 269396-56-7 ]
[1-(3,4-dichloro-benzyl)-3-oxo-3-thiazolidin-3-yl-propyl]-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4759 - 4762

15
[ 504-78-9 ]
[ 269396-59-0 ]
[1-(3,4-difluoro-benzyl)-3-oxo-3-thiazolidin-3-yl-propyl]-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide

16
[ 504-78-9 ]
[ 486459-98-7 ]
[1-(2,5-difluoro-benzyl)-3-oxo-3-thiazolidin-3-yl-propyl]-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide

17
[ 504-78-9 ]
[ 851307-12-5 ]
[1-(2,4-difluoro-benzyl)-3-oxo-3-thiazolidin-3-yl-propyl]-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide

18
[ 504-78-9 ]
[ 269396-77-2 ]
[3-oxo-3-thiazolidin-3-yl-1-(2-trifluoromethyl-benzyl)-propyl]-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide

19
[ 504-78-9 ]
[ 269726-77-4 ]
[3-oxo-3-thiazolidin-3-yl-1-(4-trifluoromethyl-benzyl)-propyl]-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide

20
[ 504-78-9 ]
[ 269726-74-1 ]
[3-oxo-3-thiazolidin-3-yl-1-(3-trifluoromethyl-benzyl)-propyl]-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide

21
[ 504-78-9 ]
[ 59969-65-2 ]
(2S,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoic acid thiazolidide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 4806 - 4820

22
[ 504-78-9 ]
[ 27486-87-9 ]
[ 311343-09-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	for 12h;	The coupling reaction of 7 (2 mmol) with thiazolidine is carried out according to method A described in the first synthetic route (example 1). After returning to ambient temperature, stirring is continued for 12 h. The reaction medium is then diluted with 50 ml of AcOEt, then washed (water, 70 ml; ice-cold saturated sodium bicarbonate, 50 ml; water, 2×50 ml), dried over sodium sulfate and evaporated to dryness under vacuum. The colorless foam obtained is subsequently purified by flash chromatography on a silica gel column (eluent: AcOEt/petroleum ether 30%). 18 is isolated in the form of a colorless gum with a yield of 80%. Rf (AcOEt/petroleum ether, 8/2): 0.40. Crystallizes from MeOH in colorless needles. M.p.=197-198 C. [alpha]D20=+0.86 (c 1.16, CHCl3) [0268] 1H NMR (CDCl3) delta ppm (isomeric mixture, 5.2/4.8: 1.95 (s, 3H, NCOCH3), 2.48-2.66 (m, 2H, CH2 cys), 2.88-3.02 (m, 2H, H5, H5' Thz), 3.24-3.34, 3.64-3.75, 3.77-3.86 (3m, 2H, H4, H4' Thz), 3.96, 4.41 and 4.45, 4.54 (2×2d, J=2×8.8 and 2×10.3 Hz, 2H, H2, H2' Thz), 4.60-4.69 (m, 1H, alpha H cys), 6.05-6.15 (m, 1H, NH cys), 7.18-7.34, 7.36-7.44 (2m, 15H, aromatic H). MS: (FAB+/G-T) m/z 953 (2M+H)+, 477 (M+H)+. Analysis: C27H28N2O2S2 (476) [TABLE-US-00051] Calc. %: C 68.07 H 5.88 N 5.88 Found %: 67.97 5.84 5.89

Reference： [1]Patent: US2004/158092,2004,A1 .Location in patent: Page 24

23
[ 504-78-9 ]
[ 81196-09-0 ]
3-[{4-(t-butoxycarbonylamino)phenyl}methylcarbonyl]thiazolidine [ No CAS ]
3-[14-(t-butoxycarbonylamino)phenyl]methylcarbonyl]thiazolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1'-carbonyldiimidazole; In tetrahydrofuran; dichloromethane; water;	40.1 3-[14-(t-butoxycarbonylamino)phenyl]methylcarbonyl]thiazolidine: 4-(t-butoxycarbonylamino)-benzeneacetic acid (1.4 g, 5.6 mmoles). intermediate 37.1. and carbonyldiimidazole (0.9 g, 5.6 mmoles) are dissolved in 15 ml of THF. The reaction is maintained at ambient temperature for 1 hour. Then thiazolidine (0.5 g, 5.6 mmol). in solution in THF (5 ml), is added to the medium. The whole is agitated again for 2 hours at ambient temperature. The solvents are evaporated off under reduced pressure. Then the residue is taken up in 25 ml of dichloromethane and washed 3 times with 15 ml of water. The organic phase is dried and concentrated under reduced pressure. 3-[{4-(t-butoxycarbonylamino)phenyl}methylcarbonyl]thiazolidine is obtained in the form of a white powder (1.43 g, 79%) and will be used without further purification in the following stages. Melting point: 223-224 C. NMR 1H (CDCl3, 100 MHz, delta): 1.51 (s, 9H, tBu), 3.00 (m, 2H, CH2-S), 3.67 (s, 2H, N-CH2-S), 3.88 (m, 2H, CH2-N), 4.52 (d, J=16 Hz, 2H, CH2-CO), 6.52 (wide s, 1H, NH), 7.26 (m, 4H, arom. H).
	With 1,1'-carbonyldiimidazole; In tetrahydrofuran; dichloromethane; water;	40.1 3-[14-(t-butoxycarbonylamino)phenyl]methylcarbonyl]thiazolidine 4-(t-butoxycarbonylamino)-benzeneacetic acid (1.4 g, 5.6 mmoles). intermediate 37.1. and carbonyldiimidazole (0.9 g, 5.6 mmoles) are dissolved in 15 ml of THF. The reaction is maintained at ambient temperature for 1 hour. Then thiazolidine (0.5 g, 5.6 mmol). in solution in THF (5 ml), is added to the medium. The whole is agitated again for 2 hours at ambient temperature. The solvents are evaporated off under reduced pressure. Then the residue is taken up in 25 ml of dichloromethane and washed 3 times with 15 ml of water. The organic phase is dried and concentrated under reduced pressure. 3-[{4-(t-butoxycarbonylamino)phenyl}methylcarbonyl]thiazolidine is obtained in the form of a white powder (1.43 g, 79%) and will be used without further purification in the following stages. Melting point: 223-224 C. NMR 1H (CDCl3, 100 MHz, delta): 1.51 (s, 9H, tBu), 3.00 (m, 2H, CH2-S), 3.67 (s, 2H, N-CH2-S), 3.88 (m, 2H, CH2-N), 4.52 (d, J=16 Hz, 2H, CH2-CO), 6.52 (wide s, 1H, NH), 7.26 (m, 4H, arom. H).

Reference： [1]Patent: US2003/78420,2003,A1
[2]Patent: US6809088,2004,B2

24
[ 504-78-9 ]
[ 18496-54-3 ]
[ 127401-86-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium chloride; triethylamine; In dichloromethane;	EXAMPLE 15 N-(4-phenylbutanoyl)thiazolidine STR12 5.5 mmol of thiazolidine and 5.5 mmol of triethylamine were dissolved in 10 ml of methylene chloride. To the solution 5 mmol of <strong>[18496-54-3]4-phenylbutanoyl chloride</strong> was added dropwise under ice-cooling with stirring. The mixture was left to raise to room temperature and further heated under refluxing for 2 hours. The resulting reaction mixture was washed with 1N hydrochloric acid, brine, and saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The solvent was evaporated by distillation and the residue was purified by column chromatography on silica gel to obtain 1.14 g of colorless crystals of N-(4-phenylbutanoyl)thiazolidine (yield: 88%). mp: below 30 C. IR (neat) cm-1: 2880-3100, 1645, 1415, 750, 700 NMR (CDCl3) δ: 1.64-2.49 (4H, m), 2.66 (2H, t, J=7 Hz), 2.80-3.14 (2H, m), 3.38-3.97 (2H, m), 4.21-4.67 (2H, m), 7.16 (5H, s)

Reference： [1]Patent: US5198450,1993,A

25
[ 504-78-9 ]
[ 336870-02-1 ]
(S)-[1-(4-hydroxy-cyclohexyl)-2-oxo-2-thiazolidin-3-yl-ethyl]-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: (S)-tert-butoxycarbonylamino-(trans-4-hydroxy-cyclohexyl)-acetic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In Isopropyl acetate at 0℃; for 2h; Stage #2: 1,3-thiazolidine In Isopropyl acetate at 0 - 20℃; for 18h;	35.B.1 Method B; Step 1: (S)-[1-(4-Hydroxy-cyclohexyl)-2-oxo-2-thiazolidin-3-yl-ethyl]-carbamic Acid tert-Butyl Ester To a suspension of 30.5 g (112 mmol) of a mixture of cis and trans Boc-L-4-hydroxycyclohexylglycine (Banfi et al. Syn. Commun. 1990, 20, 3585) and 22.0 g (123 mmol) of 2-chloro-4,6-dimethoxy-1,3,5-triazine in 380 mL of isopropyl acetate at 0° C. was added 14.8 mL (134 mmol) of 4-methylmorpholine over 1 minute. This suspension was stirred at 0° C. for 2 hours and then a solution of 10.5 g (112 mmol) of thiazolidine in 9 mL of isopropyl acetate was added over 3 minutes. The resulting suspension was warmed to room temperature and held for 18 hours. The suspension was filtered and washed two times with 200 mL of 1 N Sodium Hydroxide and 200 mL of 1 N citric acid. The organic phase was washed with brine, dried over magnesium sulfate, and concentrated in vacuo to give 35.88 g of product (93%). 1H NMR (400 MHz, CDCl3, mixture of rotamers) 5.19-5.10 (m, 1H), 4.78-4.70 (m, 0.5H), 4.64-4.62 (m, 0.5H), 4.52-4.50 (m, 1H), 4.38-4.22 (m, 1H), 4.08-4.01 (0.5H), 3.90-3.82 (0.5H), 3.72-3.68 (m, 1H), 3.57-3.48 (m, 0.5H), 3.15-3.04 (m, 1H), 2.99-2.97 (m, 1H), 2.02-1.98 (m, 1H), 1.79-1.38 (m, 14.5H), 1.26-1.09 (m, 2H). LCMS MH+=345.4.
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 12h;	1.1 (1) 4-Hydroxy-L-phenylglycine (21.56 g) was dissolved in water (250 mL) and 3 mol/L aqueous sodium hydroxide solution (43 mL). Raney-nickel (130 g) was added to conduct hydrogenation reaction under heating at 80°C and 7.0 kgf/cm2. After 3 hr, the reaction mixture was filtered, and the solid was washed with water. The filtrate was concentrated under reduced pressure to 200 mL. 1,4-Dioxane (150 mL) and triethylamine (32 mL) were added to the concentrated solution, di-tert-butyl dicarbonate (33.8 g) was added under ice-cooling, and the mixture was stirred at room temperature for 20 hr. The organic solvent was evaporated from the reaction mixture, and 2 mol/L hydrochloric acid (155 mL) was poured thereinto under ice-cooling to adjust the mixture to pH 2. Sodium chloride was added to saturation and the mixture was extracted 4 times with ethyl acetate. The extract was dried and concentrated under reduced pressure. THF (350 mL) and 1,3-thiazolidine (13.8 g) were added to the residue, HOBT (30.40 g) and EDC hydrochloride (29.7 g) were successively added under ice-cooling, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated, and saturated aqueous sodium hydrogencarbonate solution was added to the concentrate. The mixture was extracted with chloroform and the extract was dried. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography to give 3-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-1-cyclohexyl)acetyl]-1,3-thiazolidine (41.66 g, yield 93.8%) as a white solid.

Reference： [1]Current Patent Assignee: PFIZER INC - US2005/234065, 2005, A1 Location in patent: Page/Page column 24
[2]Current Patent Assignee: MITSUBISHI CHEMICAL HOLDINGS CORPORATION - EP1695969, 2006, A1 Location in patent: Page/Page column 17-18

26
[ 504-78-9 ]
[ 81196-09-0 ]
3-[{4-(t-butoxycarbonylamino)phenyl}methylcarbonyl]thiazolidine [ No CAS ]

Reference： [1]Patent: US6335445,2002,B1 .Location in patent: Page column 89

27
[ 504-78-9 ]
[ 10389-65-8 ]
[ 937207-71-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: 1,3-thiazolidine; di-t-butoxycarbonyl-L-cystine In tetrahydrofuran at 0℃; for 0.416667h; Stage #2: With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In tetrahydrofuran at 0 - 20℃; for 26h;	12.1; 1.a 440 mg (1 mmol) (Boc-Cys-OH)2 1 were dissolved in 5 ml dry THF. Under argon 158 μl (2 mmol) thiazolidine were added to the solution and after 25 min at 0° C. gradually 460 mg (2.4 mmol) N'-(3-dimethylaminopropyl)-N-ethylcarbodiimid (EDC) were added. The transformation was controlled at RT by means of thin layer chromatography (TLC). After 6 h a further activation was carried out using 460 mg (2.4 mmol) EDC and 79 μl (I mmol) thiazolidine at 0° C. After 20 h the THF was removed by distillation and the solid residue was dissolved in ethylacetate. The ethylacetate phase was rinsed 3 times with 5% KHSO4-solution, once with NaCl-solution, 3 times with saturated NaHCO3-solution and 3 times with NaCl-solution. It was dried above Na2SO4, filtrated and concentrated.The obtained raw product was purified by crystallisation from a mixture of ethylacetate/petrolether.

Reference： [1]Current Patent Assignee: IMTM - US2009/124667, 2009, A1 Location in patent: Page/Page column 25

28
[ 504-78-9 ]
[ 84624-27-1 ]
[ 518063-11-1 ]

Yield	Reaction Conditions	Operation in experiment
		1.4 g (3 mmol) <strong>[84624-27-1]Boc-Lys(Fmoc)-OH</strong> 2 and 382 mul (3 mmol) 4-ethylmorpholin were dissolved in 7 ml dry THF. The reaction batch was cooled to -15 C. and at this temperature 390 mul (3 mmol) chloroformic acid isobutyl ester were added. After a reaction time of 15 minutes at -15 C. 284 mul (3.6 mmol) thiazolidine were added, the batch was agitated for another hour at -15 C. and subsequently over night at RT.To complete the transformation half of the afore-mentioned amounts were again activated cooling the batch to -15 C. after the addition of 4-ethlymorpholine and chloroformic acid isobutyl ester and thiazolidine were added as described. After another 4 hours of reaction time at RT it was concentrated until completely dried and the residue was dissolved in ethylacetate.The ethylacetate phase was rinsed 3 times with 5% KHSO4-solution, once with NaCl-solution, 3 times with saturated NaHCO3-solution and subsequently with NaCl-solution until neutral.After drying above Na2SO4 the ethylacetate phase was concentrated and the residue was dissolved in 30 ml morpholine to cleave the Fmoc-protecting group.After 1.5 h of reaction time at RT the morpholine was removed by distillation. 6 ml ice-cold methanol were added to the residue. The solution was filtered from hardly soluble 4-fluoroene-9-ylmethylmorpholine and the solution was concentrated.Yield: 875 mg (92%) 3

Reference： [1]Patent: US2009/124667,2009,A1 .Location in patent: Page/Page column 25-26

29
[ 504-78-9 ]
[ 50-00-0 ]
[ 76-54-0 ]
[ 1306596-43-9 ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: 1,3-thiazolidine; formaldehyd In acetonitrile for 0.5h; Reflux; Stage #2: 2',7'-dichlorofluorescein In water; acetonitrile for 24h; Reflux;	13 Compound 7. Thiazolidine (0.82 g, 7.97 mmol) and paraformaldehyde (0.22 g, 7.47 mmol) were combined in 20 mL of CH3CN and refluxed for 30 min. 2,7-Dichlorofluoroscein (1.00 g, 2.49 mmol) in 30 mL of CH3CN/H2O (1:1) was added to the solution and the reaction mixture was refluxed for 24 h. The CH3CN was removed and the product and residual water were triturated with 30 mL of boiling ethanol. The product was precipitated at -25 °C, filtered on frit, washed thoroughly with ice cold water and dried. Flash chromatography on silica gel (97:3 CH2Cl2/MeOH) yielded the product as salmon pink solid (1.1 g, 73%): mp 300 °C, decompose; 1H NMR (DMSO-d6) δ 8.07 (d, 1H, J = 6.67 Hz), 7.8 (m, 2H), 7.22 (d, 1H, J = 6.74 Hz), 6.65 (s, 2H), 4.3-4.0 (m, 8H), 3.4-3.1 (m, 8H); 13C NMR (DMSO-d6) δ 168.8, 155.9, 151.4, 148.1, 135.7, 130.7, 128.2, 127.3, 125.8, 124.2, 117.7, 111.1, 109.9, 82.8, 59.0, 57.0, 49.4, 29.2; HRMS (FAB) m/z = 625.04 (M+Na)+, calcd for C28H24Cl2N2O5S2Na = 626.5263.

Reference： [1]Location in patent: experimental part Kim, Ha Na; Swamy; Yoon, Juyoung [Tetrahedron Letters, 2011, vol. 52, # 18, p. 2340 - 2343]

30
[ 504-78-9 ]
[ 22601-53-2 ]
[ 1357067-83-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: Boc-Lys(pNZ)-OH With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1h; Stage #2: 1,3-thiazolidine In dichloromethane at 0 - 20℃; for 18h;	1 70 (Scheme 10): A solution of 69 (1.0 eq.) in dichloromethane (10 ml per mmol) was cooled to 0° C. and 1-hydroxybenzotriazole (1.0 eq.) and N-(3-Dimethylaminopropyl)-N'-ethylcarbo-diimide (1.2 eq.) were added. After 1 hour at this temperature, the thiazolidine (1.2 eq.) was added and the temperature was raised to ambient temperature. The suspension was stirred for 18 hours and prior to the addition of hydrochloric acid (2 ml per mmol). The phases were separated and the aqueous layer was extracted twice with dichloromethane. The combined organic phases were dried (MgSO4) and evaporated. The crude product was purified by flash chromatography on silica (eluent: diethylether).

Reference： [1]Current Patent Assignee: IMTM - US2012/28995, 2012, A1 Location in patent: Page/Page column 77

31
[ 504-78-9 ]
[ 4530-20-5 ]
[ 15761-39-4 ]
[ 13734-41-3 ]
[ 13139-16-7 ]
[ 19746-37-3 ]
C₉H₁₇N₂O₂PolSe [ No CAS ]
[ 13836-37-8 ]
[ 73821-95-1 ]
[ 73821-97-3 ]
1,3-thiazolidine-DC(Acm)C(Acm)GERGEC(Acm)VC(Acm)GGP-C(Acm)I-[COSe-CH₂-CH₂-CO]-Ile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		1.43 g of Boc-Ile-PAM resin (0.70 mmol/g, 1 mmol) was swollenin DMF for 1 hour, after which the terminal Boc group was removedwith 2 1 min treatment with neat TFA. The resin wasflow-washed with DMF for 30 s, and neutralized with 2 1 mintreatments with 10% DIEA in DMF (v/v). The neutralized resinwas then flow washed for 30 s with DMF, then 30 s with DCM.10 equiv of DCC (2.063 g, 10 mmol) were dissolved in 5 mL ofDCM and 20 equiv of 3-iodopropionic acid (4.0 g, 20 mmol) weredissolved in 6 mL of DCM. Both solutions were cooled to 0 Cfor 5 min before being combined and allowed to react at 0 C for30 min. The resulting solution containing 3-iodopropionic anhydridewas gravity filtered to remove the dicyclohexylurea precipitate.The residue was then washed with 2 mL of DCM, filtered, andpooled with the 3-iodopropionic anhydride filtrate. The pooled filtrateswere then added to the deprotected neutralized Ile-PAM resinand allowed to couple for 45 min. The resin was drained andwashed with DCM for 30 s. Quantitative ninhydrin test indicated>99% coupling. The resin was then dried under vacuum. Yield:1.49 g (new loading: 0.661 mmol/g, 0.984 mmol) yellowish resin.550 mg (0.661 mmol/g, 0.363 mmol) of the dried acylated resinwas then swollen in 10 mL of anhydrous THF for 1 h. 5 equiv ofKSeCN (262 mg, 1.82 mmol) were added to the swollen resin inTHF. The mixture was then incubated under argon atmosphere at45 C and gently agitated for 22 h (magnetic stirring should be avoided as the stir bar will crush the resin which will later clog theSPPS synthesis vessel frits). The resin was drained and washed extensively with THF and DCM and dried under vacuum. Yield:452 mg (new loading: 0.67 mmol/g, 0.303 mmol) of greyish-whiteresin.The dried resin (450 mg, 0.3 mmol) was re-swollen in 8 mL ofTHF for 1 h, cooled to 0 C on an ice/water bath, and sodium borohydride(37.83 mg, 1 mmol) in 95% (v/v) EtOH/H2O (1 mL) wasadded in one portion. The reaction was placed at 0 C for 1 h withoccasional agitation, drained, and washed with THF, DCM, andDMF.Prior to coupling of the first amino acid, the resin was treatedwith 3 mmol 1,4-dithiothreitol (DTT) in 6 mL DMF for 10 min.The resin was then drained, and without washing, a 10 equivpre-activated mixture of Boc-Xaa-OH (3 mmol), HATU (1140 mg,3 mmol), and 1.038 mL DIEA (6 mmol) in 6 mL of DMF was addedand allowed to couple for 1 h. The resin was then drained andwashed with DMF, and the reduction and coupling steps were performeda second time. The resin was washed with DMF and stepwisesynthesis was subsequently carried out using standard Boc in-situ neutralization protocols as described previously.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 3473 - 3478

32
[ 504-78-9 ]
[ 84348-37-8 ]
[ 401564-36-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In ethyl acetate; at 2 - 7℃; for 2h;Large scale;	To (2S)-1-tert-butoxycarbonyl-4-oxopyrrolidine-2-carboxylic acid (Compound 8a) (60.0 kg),thiazolidine (30.3 kg) and N,N-diisopropylethylamine ( 118kg) in ethyl acetate and propylphosphonic anhydride (595kg) (cyclic trimer) was added 28w% at 2 -7 C in ethyl acetate (446kg) was added and the reaction mixture was 2 -4 C stirred for 2 hours. To this reaction mixture was added 15w% aqueous citric acid (600kg) for distribution, and the aqueous layer with ethyl acetate (271kg) extract. The ethyl acetate layer obtained was mixed, and sequentially washed with 10w% aqueous solution of diammoniumphosphate (600kg) and water (300kg). The ethyl acetate layer was concentrated to a residual volume 300L, n-heptane (739kg) at 23 -25 C added, and the mixture wasstirred at 23 -25 C 1 hour and stirred at 1 -5 C. The precipitated crystals were collected by filtration, with n-heptane (164 kg) were washed and driedunder reduced pressure to yield 3-[(2S)-1-tert-butoxycarbonyl-4-oxopyrrolidin-2-ylcarbonyl]thiazolidine (compound 9a) (67.8 kg, yield 86 %)
86%		(2S) -1-t-butoxycarbonyl-4-oxopyrrolidine-2-carboxylic acid (Compound 3a)(250.0 kg), N, N-diisopropylethylamine (DIPEA) (141 kg) in ethyl acetate (2242.5 kg) was added with pivaloyl chloride (131.5 kg) at 10 C. or lower, and the reaction mixture was added. The mixture was stirred at 10 C. or lower for 30 minutes.After thiazolidine (97.2 kg) was added to the reaction mixture at 10 C. or lower,The reaction mixture was stirred at 0-10 C. for 1 hour.To this reaction mixture, water (500.0 kg) was added for liquid separation,Ethyl acetate layer was prepared with diammonium hydrogen phosphate aqueous solution (prepared from 144.0 kg ammonium hydrogen phosphate and water (750.0 kg)) and saline (prepared from salt (75.0 kg) and water (425.0 kg)). Washed sequentially.After concentrating the ethyl acetate layer to a residual amount of 1250 L,2-Propanol (976.3 kg) was added and concentrated again.After the remaining amount was 1000 L, n-heptane (1368 kg) was added at 40 to 45 C., and the mixture was stirred at -5 C. or lower for 1 hour.The precipitated crystals were collected by filtration and washed with n-heptane (684.0 kg).2-Propanol (429.6 kg) was added to the obtained crystals, n-heptane (1521.9 kg) was added at 40 to 45 C., and the mixture was stirred at -5 C. or lower for 1 hour.The precipitated crystals are collected by filtration, washed with n-heptane (769.8 kg), and then dried under reduced pressure.3-[(2S) -1-t-butoxycarbonyl-4-oxopyrrolidin-2-ylcarbonyl] thiazolidine283.1 kg of (Compound 2a) was obtained.(Yield 86%)
81.7%		A solution of DCC (107.8 g) in toluene (300 mL) was added to a solution of 1-(tert-butoxycarbonyl)-4-oxo-L-proline (prepared according to the process of Example 2; 100 g) in toluene (900 mL) at -5C to - 10C, and the reaction mixture was stirred for 30 minutes at the same temperature. Dimethylaminopyridine (1 g) and thiazolidine (46.7 g) were slowly added to the reaction mixture at a temperature of about -6C to -2C over a period of about 15 to 20 minutes. The reaction mixture was allowed to warm to a temperature of 0C to 5C, and stirred at the same temperature for 60 minutes. When the reaction was complete, the reaction mixture was quenched with deionized water (20 mL), and stirred at 20C to 25C for 30 minutes. The resulting mixture was filtered through a Hyflo bed. The filtrate was washed with aqueous sodium bicarbonate solution (50 g sodium carbonate in 500 mL deionized water). The organic layer was separated and washed with an aqueous solution of sodium chloride (50 g sodium chloride in 500 mL deionized water). Activated carbon (10 g) was added to the organic layer, and the reaction mixture was stirred at 25C to 30C for 30 minutes. The reaction mixture was filtered through a Hyflo bed, and concentrated at a temperature of 50C under reduced pressure. The residue obtained was dissolved in ethyl acetate (200 mL) at 50C to 55C. Hexanes (800 mL) were added at 50C to 55C over a period of 1 to 2 hours. The reaction mixture was further cooled to a temperature of 0C to 5C, and stirred at the same temperature for 3 hours. The reaction mixture was filtered to obtain a solid. The solid was washed with a pre-cooled (0C to 5C) mixture of ethyl acetate (80 mL) and hexanes (320 mL), and dried at a temperature of 40C to 45C under reduced pressure to obtain tert-Butyl (2S)-4-oxo-2-(1.3-thiazolidin-3- ylcarbonyl)pyrrolidine-1-carboxylate. Yield: 81.7%

81.7%	With dmap; dicyclohexyl-carbodiimide; In toluene; at -6 - 5℃; for 1.33333h;	A solution of DCC (107.8 g) in toluene (300 mL) was added to a solution of 1- (tert-butoxycarbonyl)-4-oxo-L-proline (Formula V, prepared according to Example 2; 100 g) in toluene (900 mL) at -10C to -5C. The reaction mixture was stirred for 30 minutesat -10C to -5C. 4-Dimethylaminopyridine (1 g) and thiazolidine (46.7 g) were slowly added to the reaction mixture at -6C to -2C over a period of 15 minutes to 20 minutes. The reaction mixture was allowed to warm to 0C to 5C, then stirred at the same temperature for 60 minutes. When the reaction was complete, the reaction mixture was quenched with deionized water (20 mL), then stirred at 20C to 25C for 30 minutes. Theresulting mixture was filtered through a Hyflo bed. The filtrate was washed with an aqueous sodium bicarbonate solution (50 g sodium carbonate in 500 mL deionized water). The organic layer was separated, then washed with an aqueous solution of sodium chloride (50 g sodium chloride in 500 mL deionized water). Activated carbon (10 g) was added to the organic layer, then the reaction mixture was stirred at 25C to 30C for 30 minutes.The reaction mixture was filtered through a Hyflo bed, then concentrated at 50C under reduced pressure. The residue obtained was dissolved in ethyl acetate (200 mL) at 50C to 55C. Hexanes (800 mL) were added at 50C to 55C over a period of one hour to 2 hours. The reaction mixture was further cooled to 0C to 5C, then stirred at the same temperature for 3 hours. The reaction mixture was filtered to obtain a solid. The solidwas washed with a precooled (0C to 5C) mixture of ethyl acetate (80 mL) and hexanes (320 mL), then dried at 40C to 45C under reduced pressure to obtain tert-butyl (2S)-4- oxo-2-( 1,3 -thiazolidin-3 -ylcarbonyl)pyrrolidine- 1 -carboxylate.Yield: 81.7% HPLC Purity: 98.97 %
50 kg		6) Add 500 kg of toluene to a dry 2000 L reactor and add N-Boc-4-oxo-L-proline in batches.50 kg (molar amount: 229.23, molar amount: 218 mol), after stirring and dissolved, the system was cooled to below 0 C. Slowly add EDC hydrochloric acidSalt 50kg (molar amount 191.7, molar amount 261mol), and kept below 0 C for 3h;7), control system temperature below 0 C, dropwise addition of 23.4 kg of tetrahydrothiazole (molar amount 89.16, molar amount 260 mol) andA mixture of 533 g of 4-dimethylaminopyridine (molar amount 122.17, mole number 4.36) was added in about 1 h. Incubate for 1 h below 0 C;The end of the reaction of controlling N-Boc-4-oxo-L-proline in HPLC can be post-treated;8), post-treatment: the reaction solution is centrifuged, the filter cake is beaten with toluene, the organic phase is combined, 500 kg of water is added to stir, hydrochloric acid is added.Adjust the pH to about 3. The aqueous phase is separated, and the organic phase is washed with water and saturated brine, respectively, and dried and filtered;9), the organic phase is concentrated under reduced pressure at 50 C to obtain a solid and dried with an oil pump;10), the solid was recrystallized from a mixed solvent of ethyl acetate and n-hexane (ethyl acetate: n-hexane = 1:4), 250 kg.The temperature is raised from 55 C to 60 C, stirred and dissolved, and the temperature is lowered by 0 C. Centrifugation and drying gave a solid 50 kg. Yield: 76.3%. HPLC>99%, single miscellaneous <0.3%.

Reference： [1]Patent: CN103649055,2016,B .Location in patent: Paragraph 0144-0147
[2]Patent: JP2019/147763,2019,A .Location in patent: Paragraph 0082-0084; 0090-0091
[3]Patent: WO2015/19238,2015,A1 .Location in patent: Page/Page column 9; 10
[4]Patent: WO2016/79699,2016,A1 .Location in patent: Page/Page column 12
[5]Patent: CN109503567,2019,A .Location in patent: Paragraph 0023; 0029-0034; 0040-0045; 0051-0056; 0062-0066

33
[ 504-78-9 ]
[ 33996-33-7 ]
[ 1572583-20-0 ]

Yield	Reaction Conditions	Operation in experiment
33%	Stage #1: 1,3-thiazolidine; oxaceprol With 4-methyl-morpholine; benzotriazol-1-ol In dichloromethane at 0 - 5℃; for 0.5h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 25 - 30℃; for 24h;	8 1-[(2S,4R)-4-Hydroxy-2-(1,3-thiazolidin-3-ylcarbonyl)pyrrolidin-1-yl]ethanone Example 8 1-[(2S,4R)-4-Hydroxy-2-(1,3-thiazolidin-3-ylcarbonyl)pyrrolidin-1-yl]ethanone To the solution of N-acetyl-4-hydroxy-L-proline (1.5 g) in methylene dichloride (15 ml), added HOBt (0.61 g), N-methyl morpholine (1.04 g) and 1,3, thaizolidine (0.76 g) at 0-5° C. After stirring for 30 min 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.61 g) was added. The above reaction mass was stirred for 24 h at 25-30° C. Reaction mixture was evaporated under vacuum to give residue which was dissolved in sodium hydroxide solution (2.50 gm NaOH in 20 ml water). The above aqueous solution was washed with diisopropyl ether (DIPE) and separated. Resultant aqueous layer was acidified with 50% HCl aq. solution to pH 8-9. This was extracted with ethyl acetate, dried over anhydrous sodium sulphate and concentrated) under reduced pressure to obtain crude product. Purified by flash column chromatography (on silica, eluting in 35% ethylacetate in hexane) to yield title compound (0.7 g, Yield 33%). 1H NMR (300 MHz, DMSO-d6):-δ 2.07 (s, 3H), 2.19-2.30 (m, 4H), 3.31 (m, 1H), 3.50-3.53 (m, 1H), 3.79-3.84 (m, 2H), 4.18-4.21 (m, 2H), 4.49-4.77 (m, 4H)MS (m/z): 245.38

Reference： [1]Current Patent Assignee: GLENMARK PHARMACEUTICALS LTD - US9518048, 2016, B2 Location in patent: Page/Page column 28; 29

34
[ 504-78-9 ]
[ 88050-17-3 ]
3-[(2S,4R)-1-fluorenylmethoxycarbonyl-4-hydroxy-2-pyrrolidinylcarbonyl]1,3-thiazolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 3 Synthesis of 3-[(2S,4R)-1-fluorenylmethoxycarbonyl-4-hydroxy-2-pyrrolidinylcarbonyl]1,3-thiazolidine. To a solution of Example-2 compound (100 g) in methylene dichloride (MDC) (500 ml) was added HOBT (hydroxybenzotriazole) (19.11 g), N-methyl morpholine (28.63g) and 1,3 thaizolidine (example-1 compound) (25.23 g) at 0-5 C. After stirring for 30 min 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (65.2 g) was added. The above reaction mass was further stirred for 24 hr at 25-30 C. The reaction mixture was monitored by TLC (thin layer chromatography). The reaction mass was then evaporated under reduced pressure. Sodium hydroxide solution (22.64 gm NaOH in 500 ml water) was added to the obtained oily residue. The above aqueous solution was washed with DIPE (diisopropyl ether). Then the pH of aqueous solution was adjusted to 8-9 by 50% HCl aq. solution. The above solution was extracted with ethyl acetate and dried over anhydrous sodium sulphate and concentrated under reduced pressure. The obtained oily compound was crystallised from IPA to yield 55.0 g of title compound as off white solid. 1H NMR (300 MHz, DMSO-d6):-delta 1.85-1.89 (m,1H), 2.17-2.20 (m, 1H), 2.91-3.10 (m, 2H), 3.35-3.63 (m, 5H), 4.17-4.38 (m, 5H), 4.45-4.74 (m,2H), 5.1 (d, 1H), 7.31-7.42 (m, 4H), 7.56-7.65 (m, 2H), 7.87-7.91 (m, 2H). Mass-(M+H):-425.18.

Reference： [1]Patent: US9518048,2016,B2 .Location in patent: Page/Page column 24; 25

35
[ 504-78-9 ]
[ 1877-71-0 ]
methyl 3-(thiazolidine-3-carbonyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 18h;	35 A mixture of thiazolidine (500 mg, 2.77 mmol), HATU (i.26g, 3.32 mmol), 3- (methoxycarbonyl)benzoic acid (235mg, 2.63 mmol) and DIPEA (i.07g, 8.3i mmol) in DMF (10 ml) was stirred at room temperature for i8h. The mixture was then diluted with water and ethyl acetate. Organic layer was washed with saturated aqueous sodium bicarbonate, water, brine and dried. Crude residue was purified by column chromatography to yield methyl 3-(thiazolidine-3-carbonyl)benzoate in 85% yield.

Reference： [1]Current Patent Assignee: JORTAN PHARMACEUTICALS - WO2017/66742, 2017, A1 Location in patent: Paragraph 0108; 0109

36
[ 504-78-9 ]
[ 315-14-0 ]
3-(3',5'-difluoro-4'-nitrophenyl)thiazolidine [ No CAS ]
3-(3',5'-difluoro-2'-nitrophenyl)thiazolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%		To a solution of <strong>[315-14-0]2,4,6-trifluoronitrobenzene</strong> (1) (7.084 g,40.0 mmol) in dry dimethylformamide (40 mL) was addedpotassium carbonate (6.63 g, 48.0 mmol, 1.2 equiv.) and the mixture cooled in an ice/water bath and stirred under argon. A solution of thiazolidine (3.575 g, 40.0 mmol) in dry DMF(10 mL) was then added slowly by pipette over 5 min. After 10 min the ice/water bath was removed and the mixture stirred atroom temperature under argon for 94 h. The solvent was then removed by rotary evaporator and the residue partitioned between ethyl acetate (80 mL) and water (80 mL). The aqueous layer was extracted with additional ethyl acetate (280 mL)and the combined organic extract washed with brine (150 mL),dried (MgSO4), and evaporated to give a yellow-orange crystalline mass (9.39 g). The solid was triturated with 10% dichloromethane in petroleum spirit (256 mL) and the combined yellow supernatants evaporated to give 4.4 g of material enriched in the desired ortho isomer. The material was dissolvedin 2 : 1 petroleum spirit/dichloromethane, applied to a 80 g silicagel cartridge over multiple runs, and eluted with a dichloromethane/petroleum spirit profile to give 3-(30,50-difluoro-20-nitrophenyl)thiazolidine (2c) as a viscous yellow oil thatsolidified on standing (3.07 g, 31 %), mp 47-498C. dH(500 MHz, CDCl3) 3.06 (t, J 6.5, 2H, H5), 3.56 (t, J 6.5, 2H, H4),4.36 (s, 2H, H2), 6.52 (ddd, J 9.5, 8.0, 2.5, 1H, H40), 6.66 (app dt,J 11.0, 2.0, 1H, H60). dC (125 MHz, CDCl3) 30.4 (C5), 54.5, 54.6(C2, C4), 96.7 (dd, 2JCF 24, 2JCF 25, C40), 101.0 (dd, 2JCF 25,4JCF 3, C60), 143.7 (dd, 3JCF 12, 3JCF 3, C10), 156.1 (dd, 1JCF 265,3JCF 16, C30 or C50), 163.3 (dd, 1JCF 251, 3JCF 15, C50 or C30). C20 was not observed. m/z (ESI ve) 247 ([M H], 100 %).HRMS (ESI ve) m/z 247.03474; C9H9F2N2O2S requires247.03473 (D0.0 ppm).The insoluble orange solid from the trituration (4.8 g) wasshown by 1H NMR analysis to be a 9 : 1 mixture of 3c/2c. In aseparate preparation the slower eluting 3-(30,50-difluoro-40-nitrophenyl)thiazolidine (3c) was collected during chromatographyand had the following data: mp 101-1048. dH (500 MHz,CDCl3) 3.21 (t, J 6.5, 2H, H5), 3.67 (t, J 6.5, 2H, H4), 4.42(s, 2H, H2), 6.19 (m, 2H, H20/60).

Reference： [1]Australian Journal of Chemistry,2019,vol. 72,p. 311 - 327

37
[ 504-78-9 ]
[ 578-22-3 ]
(5-hydroxy-2-methylphenyl)(thiazolidin-3-yl)methanone [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 2412 - 2415

38
[ 504-78-9 ]
[ 102195-80-2 ]
[ 401564-36-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With acetic acid; In methanol; at 0 - 30℃; for 2.5h;Large scale;	Add 1500 Kg of methanol to the reaction kettle.250Kg compound 3-1, acetic acid 6.4Kg,Then, the temperature was lowered to 0 to 5 C, and then 96 kg of tetrahydrothiazole was added dropwise to the reaction vessel at an internal temperature of not more than 10 C.After the completion of the dropwise addition, the reaction was kept at 0 to 5 C for 2 h, and then raised to 30 C for 0.5 h.After the reaction is completed, the mixture is concentrated under reduced pressure until solvent-free evaporation.Add 1500 Kg of dichloromethane, 300 Kg of saturated sodium bicarbonate solution to the reaction kettle, and stir for 30 minutes.After standing for 30 minutes, the layers were separated, and the organic layer was washed twice with 150 Kg of brine.The organic phase was concentrated under reduced pressure to give a pale yellow solid.The crude product was then dissolved in 280 kg of ethyl acetate.Heat to 50 ~ 55 C, dissolve, add 1120Kg petroleum ether to the reaction kettle, add dropwise,Slowly cool to 0 ~ 5 C, and crystallization at 0 ~ 5 C for 30 minutes.After centrifugation, the solid was washed with a petroleum ether: ethyl acetate (4:1) mixed solution of 100 Kg.Drying at 45 to 50 C gives 278 Kg of compound 4-1.The yield was 90%.

Reference： [1]Patent: CN110294748,2019,A .Location in patent: Paragraph 0034-0036

39
[ 504-78-9 ]
[ 6065-32-3 ]
ethyl 4-(thiazolidin-3-yl)but-2-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10.1 g	With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 16h;	2 Step 2: To a solution of thiazolidine (5.6 g, 62.7 mmol) and DIPEA (18.8 mL,1 14 mmol) in THF (120 mL) was added ethyl 4-bromobut-2-enoate 50 (1 1 g, 57 mmol) at rt. The reaction mixture was stirred at rt for 16 h. The reaction mixture was filtered and the filtrate was diluted with EtOAc (100 mL). The solution was washed with water, then with brine, dried and concentrated. The crude compound was purified by silica gel column chromatography (PE/EtOAc: 10:1 to 5:1 ) to give ethyl 4-(thiazolidin-3-yl)but-2-enoate 51 (10.1 g, 50 mmol) as a light yellow oil. (0515) [0313] LCMS: (M+1 )+ = 202; Retention time = 1.41 min. CP Method C1

Reference： [1]Current Patent Assignee: ARKUDA THERAPEUTICS - WO2020/252222, 2020, A1 Location in patent: Paragraph 0312-0313

40
[ 504-78-9 ]
[ 1518-16-7 ]
2-(4-(cyano(thiazolidin-3-yl)methylene)cyclohexa-2,5-dien-1-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol at 20℃;	2.3. Spectrophotometric titrations General procedure: The spectrophotometric titration study was performed between selected three π acceptors (CHL, DDQ and TCNQ) and the thiazolidine (TZD) in situ methanol solvent at room temperature. The concentration of the TZD donor in the reaction mixtures was kept fixed at 10-4 M while the π acceptors (CHL, DDQ and TCNQ) changed over a wide range of concentrations 0.25 3.0 × 10-4 M with molar ratio (1.0:0.25) to (1.0: 3.0) (donor: acceptor). The maximum absorbance peaks of the resulted charge transfer complexes at 364 nm for [(TZD)(DDQ)], 436 nm for [(TZD)(CHL)], and 477 nm for [(TZD)(TCNQ)] were measured for each mixture and plotted as a function of the CHL, DDQ or TCNQ acceptors to TZD donor molar ratio. The stoichiometry of the molecular charge transfer complexes under investigation were determined by the application of the conventional spectrophotometricmolar ratio according to Skoog methods and were also used to obtain the modified Benesi-Hildebrand plots in order to calculatethe formation constant, K, and the molar extinction, ε, values for each charge transfer complexes.

Reference： [1]Al-Humaidi, Jehan Y.; El-Sayed, Mohamed Y.; Refat, Moamen S.; Altalhi, Tariq A.; Eldaroti, Hala H. [Journal of Molecular Liquids, 2021, vol. 333]

41
[ 504-78-9 ]
[ 312300-42-8 ]
3-((6-methoxypyridin-3-yl)sulfonyl)thiazolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77.7%	With dmap; triethylamine In dichloromethane at 25℃;	28 Production of 3-((6-methoxypyridin-3-yl)sulfonyl)thiazolidine Reference Example 28 Production of 3-((6-methoxypyridin-3-yl)sulfonyl)thiazolidine To a solution of 2-methoxypyridine-5-sulfonyl chloride (100 mg, 0.48 mmol, 1.0 equiv) in CH2Cl2 (5.0 mL) was added thiazolidine (37.8 μL, 0.48 mmol, 1.0 equiv), N,N-dimethyl-4-aminopyridine (58.6 mg, 0.48 mmol, 1.0 equiv), and triethylamine (10 μL, 0.076 mmol, 1.0 equiv). The mixture was stirred at room temperature overnight. The resulting mixture was extracted with EtOAc, and the combined organic layer was washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography (MeOH/EtOAc = 30%) to give 3-((6-methoxypyridin-3-yl)sulfonyl)thiazolidine as a brown solid (151 mg, 0.504 mmol, 77.7% yield). 1H NMR (500 MHz, CDCl3) δ 8.64 (d, J = 1.5 Hz, 1H), 7.94-7.96 (m, 1H), 6.82 (d, J = 8.0 Hz, 1H), 4.44-4.50 (m, 2H), 4.01 (s, 3H), 3.62-3.65 (m, 2H), 2.77-2.81 (m, 2H).

Reference： [1]Current Patent Assignee: KYUSHU UNIVERSITY - EP3888651, 2021, A1 Location in patent: Paragraph 0152; 0220; 0221

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Thiazolidines

[ 14446-47-0 ]

Thiazolidine hydrochloride

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