[ CAS No. 52499-14-6 ] {[proInfo.proName]}

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Quality Control of [ 52499-14-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 52499-14-6 ]

CAS No. :	52499-14-6	MDL No. :	MFCD00961845
Formula :	C₁₈H₂₉ClO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	344.94	Pubchem ID :	-
Synonyms :

Safety of [ 52499-14-6 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P501-P260-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405	UN#:	3261
Hazard Statements:	H314-H290	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 52499-14-6 ]

* 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 [ 52499-14-6 ]
Downstream synthetic route of [ 52499-14-6 ]

[ 52499-14-6 ] Synthesis Path-Upstream 1~1

1
[ 4005-51-0 ]
[ 52499-14-6 ]
[ 1191951-57-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 6, p. 2046 - 2054
[2] Patent: WO2009/129267, 2009, A2, . Location in patent: Page/Page column 85

[ 52499-14-6 ] Synthesis Path-Downstream 1~9

1
[ 52499-14-6 ]
[ 171754-03-3 ]
(1S,3R,4R)-2-(4-Dodecyl-benzenesulfonyl)-2-aza-bicyclo[2.2.1]heptane-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With sodium carbonate In tetrahydrofuran at 25℃; for 72h;

Reference： [1]Hodgson, David M.; Stupple, Paul A.; Pierard, Francoise Y. T. M.; Labande, Agnes H.; Johnstone, Craig [Chemistry - A European Journal, 2001, vol. 7, # 20, p. 4465 - 4476]

2
[ 14949-00-9 ]
[ 52499-14-6 ]
[ 1191951-78-6 ]

Yield	Reaction Conditions	Operation in experiment
63%	With triethylamine In acetonitrile at 20℃; for 48h;	2.1.16. 5-(4-Dodecylphenylsulfonamido)-1,3,4-thiadiazole-2-sulfonamide (40) A suspension of 5-amino-1,3,4-thiadiazolo-2-sulfonamide32 (4.10 g, 22.8 mmol) in anhydrous acetonitrile (100 mL) was stirred and cooled in an ice bath. Triethylamine (2.5 g, 25 mmol) and a solution of p-dodecylbenzenesulfonyl chloride (8.6 g, 25 mmol) in anhydrous acetonitrile (60 mL) were added, the reaction mixture allowed to attain rt, and then stirred for 48 h. Volatiles were removed in vacuo and the residue was washed with 10% aqueous HCl (100 mL) and water (100 mL) in order to eliminate salts. The residue was subjected to chromatography on silica gel (70-230 mesh) eluted with CH2Cl2/MeOH 19:1 to give the product 40 (7.0 g, 14.3 mmol, 63%), Rf 0.56 (10% MeOH/CH2Cl2). Recrystallization from absolute ethanol and a second chromatography gave an analytical sample, mp 249-250 °C; 1H NMR (300 MHz, DMSO-d6) δ 0.85 (3, t, J = 6.6 Hz), 1.23 (18, m), 1.55 (2, m), 2.58 (2, t, J = 7.2 Hz), 7.23 (2, d, J = 7.8 Hz), 7.34 (2, s), 7.59 (2, d, J = 8.1 Hz); 13C NMR (75 MHz, DMSO-d6) δ 13.9, 22.1, 28.7, 28.9, 29.0, 29.1, 30.8, 31.3, 34.9, 126.2, 127.8, 143.3, 145.1, 161.2, 170.9; HRMS (ESI-, m/z) calcd for C20H31N4O4S3 487.1513, observed 487.1514 (M-H)-.
39%	With triethylamine In acetonitrile at 0 - 20℃;	1 5- Amino-l,3,4-thiadiazolo-2-sulfonamide (200 mg, 1.1 mmol) was suspended in anhydrous acetonitrile (5 mL). Triethylamine (123 mg, 1.2 mmol) was added with stirring at 0 0C followed by a solution of 4-dodecylbenzenesulfonyl chloride (383 mg, 1.1 mmol) in anhydrous acetonitrile (3 mL). The reaction mixture was stirred overnight at room temperature. Volatiles were then removed in vacuo and the residue was washed with water (5 mL) in order to eliminate the ammonium salt. The crude solid was subjected to chromatography on silica gel (70-230 mesh) eluted with CH2Cl2 methanol 19:1 to give the product in 39% yield. Recrystallization from absolute ethanol and a second round of chromatography gave an analytic sample, mp 249-250 0C; 1H NMR (300 MHz, OMSO-d6) δ 0.85 (t, 3H, J = 6.6 Hz), 1.23 (m, 18H), 1.55 (m, 2H), 2.58 (t, 2H, J = 7.2 Hz), 7.23 (d, 2H, J = 7.8 Hz), 7.34 (s, 2H), 7.59 (d, 2H, J = 8.1 Hz); 13C NMR (75 MHz, OMSO-d6) δ 13.9, 22.1, 28.7, 28.9, 29.0, 29.1, 30.8, 31.3, 34.9, 126.2, 127.8, 143.3, 145.1, 161.2, 170.9; LRMS (LCQ, ESl") calcd for C20H3IN4O4S3 487.2, found 487.1 (M-H)"; HRMS (ESl", m/z) calcd for C20H3IN4O4S3 487.1513, found 487.1514 (M-H)".

Reference： [1]Location in patent: experimental part Ahad, Ali Md.; Zuohe, Song; Du-Cuny, Lei; Moses, Sylvestor A.; Zhou, Li Li; Zhang, Shuxing; Powis, Garth; Meuillet, Emmanuelle J.; Mash, Eugene A. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 6, p. 2046 - 2054]
[2]Current Patent Assignee: THE UNIVERSITY OF TEXAS SYSTEM; ARIZONA BOARD OF REGENTS - WO2009/129267, 2009, A2 Location in patent: Page/Page column 98-99

3
[ 64837-53-2 ]
[ 52499-14-6 ]
[ 1191951-63-9 ]

Yield	Reaction Conditions	Operation in experiment
78%	With pyridine; at 20 - 95℃; for 48.25h;	General procedure: A suspension of ethyl 2-(5-amino-1,3,4-thiadiazol-2-yl)acetate29 (2.0 g, 11.2 mmol) in pyridine (50 mL) was stirred and cooled in an ice bath while p-dodecylbenzenesulfonyl chloride (4.7 g, 13.5 mmol) was added slowly. The mixture was stirred at rt for 48 h, then heated in an oil bath at 90 °C for 15 min. The reaction mixture was then cooled to rt, poured into aqueous 10percent HCl, and extracted with EtOAc (3 .x. 75 mL). The combined extracts were washed with water (2 .x. 50 mL), brine (2 .x. 50 mL), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was subjected to chromatography on silica gel (70-230 mesh) eluted with CH2Cl2/MeOH 95:5 to give the product 37 (2.9 g, 5.9 mmol, 53percent)
34%	With pyridine; at 20℃; for 4.5h;	To a solution of /?-dodecylbenzenesulfonyl chloride (260 mg, 0.75 mmol) in pyridine (3 mL) was added ethyl 5-amino-l,3,4-thiadiazole-2-carboxylate (100 mg, 0.58 mmol). The reaction mixture was stirred at room temperature for 4.5 h, then 2 M HCl was added to quench the reaction. The mixture was extracted with ethyl acetate (3 x 40 mL). The organic extracts were washed with water (20 mL), brine (20 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography over silica gel (70-230 mesh) eluted with CH2Cl2 methanol 49:1 to give the product as a solid, mp 96-97 0C, in 34percent yield (95 mg, 0.20 mmol); 1H NMR (300 MHz, CDCl3) delta 0.85 (t, 3H, J = 6.6 Hz), 1.20-1.35 (m, <n="90"/>21H), 1.57 (m, 2H), 2.60 (t, 2H, J = 7.0 Hz), 4.43 (q, 2H, J = 7.2 Hz), 7.26 (d, 2H, J = 8.0 Hz), 7.77 (d, 2H, J = 7.7 Hz); 13C NMR (300 MHz, CDCl3) delta 14.1, 22.7, 29.3, 29.4, 29.6, 29.6, 31.1, 31.9, 35.9, 63.4, 126.6, 128.9, 136.9, 145.8, 159.9, 163.7, 167.9; MS (LCQ, ESI+) Calcd for C23H36N3O4S2 482.2, found 482.1 (M+H)+; HRMS (ESI+, m/z) Calcd for C23H36N3O4S2 482.2140, found 482.2134 (M+H)+.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2046 - 2054
[2]Patent: WO2009/129267,2009,A2 .Location in patent: Page/Page column 88-89

4
[ 4005-51-0 ]
[ 52499-14-6 ]
[ 1191951-57-1 ]

Yield	Reaction Conditions	Operation in experiment
51%	With pyridine
	With pyridine at 0 - 95℃;	1 2-Amino- 1,3,4-thiadiazole (439 mg, 4.3 mmol) was suspended in pyridine (1.5 mL). p- Dodecylbenzenesulfonyl chloride (1.0 mg, 2.9 mmol) was added slowly at 0 0C. The reaction mixture was then heated to 95 0C and was stirred at this temperature for 1 h. The reaction mixture was then added to aqueous 10% HCl (15 mL) and the resulting mixture extracted with ethyl acetate (3 x 30 mL). The organic extracts were washed with water (3 x 50 mL), brine (3 x 50 mL), dried over anhydrous Na2SO4, filtered, and volatiles evaporated to yield a solid mass. Chromatography on silica gel (70-230 mesh) eluted with 2% MeOH in CH2Cl2 gave the product (600 mg, 1.5 mmlo, 51%). Recrystallization from hexanes:ethyl acetate (3:7) gave an analytical sample, mp 126-127 0C; 1H NMR (500 MHz, CDCl3) δ 0.87 (3, t, J = 6.5 Hz), 1.20-1.36 (18, m), 1.54-1.63 (2, m), 2.62 (2, t, J = 7.5 Hz), 7.25 (2, d, J = 8.0 Hz), 7.83 (2, d, J = 8.0 Hz), 8.28 (1, s), 12.81 (1, br s); 13C NMR (125 MHz, CDCl3) δ 14.0, 22.6, 29.2, 29.3, 29.4, 29.5, 29.6, 31.0, 31.8, 35.8, 126.4, 128.9, 138.0, 142.8, 148.5, 167.5; MS (LCQ, ESI+) Calcd for C20H32N3O2S2 410.1936, found 410.10 (M+H)+; HRMS (ESI+, m/z) Calcd C20H32N3O2S2 410.1936, found 410.1932 (M + H)+.

Reference： [1]Location in patent: scheme or table Ahad, Ali Md.; Zuohe, Song; Du-Cuny, Lei; Moses, Sylvestor A.; Zhou, Li Li; Zhang, Shuxing; Powis, Garth; Meuillet, Emmanuelle J.; Mash, Eugene A. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 6, p. 2046 - 2054]
[2]Current Patent Assignee: ARIZONA BOARD OF REGENTS; THE UNIVERSITY OF TEXAS SYSTEM - WO2009/129267, 2009, A2 Location in patent: Page/Page column 85

5
[ 14068-53-2 ]
[ 52499-14-6 ]
[ 1191951-59-3 ]

Yield	Reaction Conditions	Operation in experiment
59%	With pyridine at 95℃; for 1h;	2.1.10. 4-Dodecyl-N-(5-ethyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide (34) General procedure: A suspension of 2-amino-5-methyl-1,3,4-thiadiazole (150 mg, 1.3 mmol) in pyridine (0.5 mL) was stirred and cooled in an ice bath while p-dodecylbenzenesulfonyl chloride (300 mg, 0.87 mmol) was added slowly. The reaction mixture was allowed to attain rt, then heated in an oil bath at 95 °C for 1 h. The reaction mixture was then cooled, added to aqueous 10% HCl (5 mL), and the resulting mixture extracted with EtOAc (3 × 10 mL). The organic extracts were washed with water, brine, dried over anhydrous Na2SO4, filtered, and volatiles evaporated in vacuo to yield a solid mass. Chromatography on silica gel (70-230 mesh) eluted with CH2Cl2/MeOH 49:1 gave the product 33 (310 mg, 0.73 mmol, 84%),
59%	With pyridine at 0 - 95℃;	1 - Amino-5-ethyl-l,3,4-thiadiazole (169 mg, 1.3 mmol) was suspended in pyridine (0.5 mL). p- Dodecylbenzenesulfonyl chloride (300 mg, 0.87 mmol) was added slowly at 0 0C. The reaction mixture was then heated to 95 0C and was stirred at this temperature for 1 h. The reaction mixture was then added to aqueous 10% HCl (5 mL) and the resulting mixture extracted with ethyl acetate (3 x 10 mL). The organic extracts were washed with water, brine, dried over anhydrous Na2SO4, filtered, and volatiles evaporated to yield a solid mass. Chromatography on silica gel (70-230 mesh) eluted with 2% MeOH in CH2Cl2 gave the product (225 mg, 0.51 mmol, 59%). Recrystallization from hexanes:ethyl acetate (3:7) gave an analytical sample, mp 93-94 0C; 1H NMR (500 MHz, CDCl3) δ 0.88 (3, t, J = 6.5 Hz), 1.20-1.36 (18, m), 1.33 (3, t, J= 7.5 Hz), 1.54-1.63 (2, m), 2.63 (2, t, J= 7.5 Hz), 2.84 (2, q, J = 7.5 Hz), 7.25 (2, d, J = 8.5 Hz), 7.83 (2, d, J = 8.5 Hz), 12.30 (1, br s); 13C NMR (125 MHz, CDCl3) δ 12.6, 14.1, 22.7, 24.4, 29.2, 29.3, 29.4, 29.5, 29.6, 31.1, 31.9, 35.9, 126.5, 128.8, 138.4, 148.2, 160.1 168.2; MS (ESI+, m/z) Calcd for C22H36N3O2S2 438.2249, found 438.30 (M+H)+; HRMS (ESI+, m/z) Calcd for C22H36N3O2S2 438.2249, found 438.2247 (M + H)+.

6
[ 39222-73-6 ]
[ 52499-14-6 ]
[ 1191951-60-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	With pyridine; at 0 - 95℃;	2-Amino-5-ter£-butyl-l,3,4-thiadiazole (204 mg, 1.3 mmol) was suspended in pyridine (0.5 mL). /?-Dodecylbenzenesulfonyl chloride (300 mg, 0.87 mmol) was added slowly at 0 0C. The reaction mixture was then heated to 95 0C and was stirred at this temperature for 1 h. The reaction mixture was then added to aqueous 10% HCl (5 mL) and the resulting mixture extracted with ethyl acetate (3 x 10 mL). The organic extracts were washed with water, brine, dried over anhydrous Na2SO4, filtered, and volatiles evaporated to yield a solid mass. Chromatography on silica gel (70-230 mesh) eluted with 2% MeOH in CH2Cl2 gave the product (350 mg, 0.75 mmol, 87%). Recrystallization from hexanes:ethyl acetate (3:7) gave an analytical sample, mp 117-118 0C; 1H NMR (500 MHz, CDCl3) delta 0.88 (3, t, J = 6.5 Hz), 1.20-1.36 (18, m), 1.38 (9, s), 1.56-1.64 (2, m), 2.63 (2, t, J= 7.5 Hz), 7.25 (2, d, J = 8.0 Hz), 7.86 (2, d, J = 8.0 Hz), 12.24 (1, br s); 13C NMR (125 MHz, CDCl3) delta 14.1, 22.7, 29.2, 29.3, 29.4, 29.5, 29.6, 29.7, 31.1, 31.8, 35.8, 36.5, 126.5, 128.7, 138.5, 148.1, 167.8, 168.0; MS (ESI+, m/z) Calcd for C24H40N3O2S2 466.3, found 466.2 (M+H)+; HRMS (ESI+, m/z) Calcd for C24H40N3O2S2 466.2562, found 466.2562 (M + H) N++.
86%	With pyridine; at 95℃; for 1h;	General procedure: A suspension of 2-amino-5-methyl-1,3,4-thiadiazole (150 mg, 1.3 mmol) in pyridine (0.5 mL) was stirred and cooled in an ice bath while p-dodecylbenzenesulfonyl chloride (300 mg, 0.87 mmol) was added slowly. The reaction mixture was allowed to attain rt, then heated in an oil bath at 95 C for 1 h. The reaction mixture was then cooled, added to aqueous 10% HCl (5 mL), and the resulting mixture extracted with EtOAc (3 × 10 mL). The organic extracts were washed with water, brine, dried over anhydrous Na2SO4, filtered, and volatiles evaporated in vacuo to yield a solid mass. Chromatography on silica gel (70-230 mesh) eluted with CH2Cl2/MeOH 49:1 gave the product 33 (310 mg, 0.73 mmol, 84%),

Reference： [1]Patent: WO2009/129267,2009,A2 .Location in patent: Page/Page column 87
[2]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2046 - 2054

7
[ 52499-14-6 ]
[ 56951-58-7 ]
[ 1191951-64-0 ]

Yield	Reaction Conditions	Operation in experiment
65%	With pyridine; at 20 - 95℃; for 48.25h;	General procedure: A suspension of ethyl 2-(5-amino-1,3,4-thiadiazol-2-yl)acetate29 (2.0 g, 11.2 mmol) in pyridine (50 mL) was stirred and cooled in an ice bath while p-dodecylbenzenesulfonyl chloride (4.7 g, 13.5 mmol) was added slowly. The mixture was stirred at rt for 48 h, then heated in an oil bath at 90 C for 15 min. The reaction mixture was then cooled to rt, poured into aqueous 10% HCl, and extracted with EtOAc (3 × 75 mL). The combined extracts were washed with water (2 × 50 mL), brine (2 × 50 mL), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was subjected to chromatography on silica gel (70-230 mesh) eluted with CH2Cl2/MeOH 95:5 to give the product 37 (2.9 g, 5.9 mmol, 53%)
65%	at 20℃; for 4.5h;	To a solution of /?-dodecylbenzenesulfonyl chloride (200 mg, 0.58 mmol) in pyridine (3 rnL) was added 2-amino-5-hydroxymethyl-l,3,4-thiadiazole (70 mg, 0.53 mmol). The reaction mixture was stirred at room temperature for 4.5 h, then 2 M HCl (8 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate (3 x 20 mL). The organic extracts were washed with water (10 mL), brine (10 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography on silica gel (70-230 mesh) eluted with CH2Cl2 methanol 19:1 to give the product as a solid, mp 138-139 C, in 65% yield (151 mg, 0.34 mmol); 1H NMR (300 MHz, DMSO-^) delta 0.84 (t, 3H, J = 6.6 Hz), 1.22 (m, 18H), 1.54-1.57 (m, 2H), 2.64 (t, 2H, J = 7.8 Hz), 4.57 (s, 2H), 6.05 (br, IH), 7.35 (d, 2H, J = 8.1 Hz), 7.67 (d, 2H, J = 7.8 Hz); 13C NMR (75 MHz, DMSO-^) delta 13.9, 22.1, 28.6, 28.7, 28.8, 29.0, 30.6, 31.3, 34.9, 58.4, 125.8, 128.9, 139.2, 147.5, 161.1, 167.5; MS (LCQ, ESI+) Calcd for C2IH34N3O3S2 440.2, found 440.2 (M+H)+; HRMS (ESI+, m/z) Calcd for C21H34N3O3S2 440.2042, found 440.2029 (M+H)+.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2046 - 2054
[2]Patent: WO2009/129267,2009,A2 .Location in patent: Page/Page column 89

8
[ 88124-55-4 ]
[ 52499-14-6 ]
[ 1191951-62-8 ]

Yield	Reaction Conditions	Operation in experiment
53%	With pyridine at 20 - 95℃; for 48.25h;	2.1.13. Ethyl 2-(5-(4-Dodecylphenylsulfonamido)-1,3,4-thiadiazol-2-yl)acetate (37) A suspension of ethyl 2-(5-amino-1,3,4-thiadiazol-2-yl)acetate29 (2.0 g, 11.2 mmol) in pyridine (50 mL) was stirred and cooled in an ice bath while p-dodecylbenzenesulfonyl chloride (4.7 g, 13.5 mmol) was added slowly. The mixture was stirred at rt for 48 h, then heated in an oil bath at 90 °C for 15 min. The reaction mixture was then cooled to rt, poured into aqueous 10% HCl, and extracted with EtOAc (3 × 75 mL). The combined extracts were washed with water (2 × 50 mL), brine (2 × 50 mL), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was subjected to chromatography on silica gel (70-230 mesh) eluted with CH2Cl2/MeOH 95:5 to give the product 37 (2.9 g, 5.9 mmol, 53%), Rf 0.64 (10% MeOH/CH2Cl2). Recrystallization from EtOAc/hexanes gave an analytical sample, mp 110-111 °C; 1H NMR (500 MHz, CDCl3) δ 0.88 (3, t, J = 7.0 Hz), 1.20-1.28 (18, m), 1.32 (3, t, J = 7.0 Hz), 1.58-1.66 (2, m), 2.64 (2, t, J = 7.0 Hz), 3.87 (2, s), 4.25 (2, q, J = 7.0 Hz), 7.26 (2, d, J = 8.0 Hz), 7.82 (2, d, J = 8.0 Hz), 10.91 (1, br s); 13C NMR (125 MHz, CDCl3) δ 14.0, 14.1, 22.6, 29.2, 29.3, 29.4, 29.5, 29.6, 31.1, 31.9, 35.9, 36.4, 62.2, 126.4, 128.8, 138.2, 148.3, 151.2, 167.3, 168.6; HRMS (ESI+, m/z) calcd for C24H38N3O4S3 496.2304, observed 496.2295 (M+H)+.
43%	With pyridine at 20℃; for 4.5h;	1 To a solution of/?-dodecylbenzenesulfonyl chloride (1.01 g, 2.94 mmol) in pyridine (10 rnL) was added ethyl 2-(5-amino-l,3,4-thiadiazol-2-yl)acetate (500 mg, 2.67 mmol). The reaction mixture was stirred at room temperature for 4.5 h, then 2 M HCl (20 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate (3 x 50 mL). The organic extracts were washed with water (20 mL), brine (20 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography over silica gel (70-230 mesh) eluted with CH2Cl2 methanol 19:1 to give the product as a solid, mp 108-109 0C, in 43% yield (570 mg, 1.15 mmol); 1H NMR (300 MHz, CDCl3) δ 0.87 (t, 3H, J = 7.2Hz), 1.24-1.34 (m, 21H), 1.55-1.66 (m, 2H), 2.63 (t, 2H, J = 7.2 Hz), 3.88 (s, 2H), 4.25 (q, 2H, J = 7.5 Hz), 7.25 (d, 2H, J = 8.1 Hz), 7.81 (d, 2H, J = 7.8 Hz); 13C NMR (75 MHz, CDCl3) δ 14.0, 14.1, 22.7, 29.3, 29.5, 29.6, 29.7, 31.2, 31.9, 35.9, 38.1, 61.9, 126.7, 128.4, 138.8, 147.2, 152.1, 168.3, 170.3; MS (LCQ, ESI+) Calcd for C24H38N3O4S2 496.2, found 496.2 (M+H)+; HRMS (ESI+, m/z) Calcd for C24H38N3O4S2 496.2304, found 496.2295 (M+H)+.

9
[ 87-89-8 ]
[ 52499-14-6 ]
DL-1-O-p-dodecylbenzenesulfonyl-myo-inositol [ No CAS ]
[ 1448044-01-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 66% 2: 16%	Stage #1: D-myo-inositol; p-dodecylbenzenesulfonyl chloride With triethylamine; lithium chloride In N,N-dimethyl acetamide at 20℃; Stage #2: With pyridine; chloro-trimethyl-silane In methanol; N,N-dimethyl acetamide at 20℃; for 3h; Stage #3: With trifluoroacetic acid In methanol; chloroform at 20℃; for 2h;	4.4 Representative procedure for synthesis of 1-O-substituted dl-myo-inositol: synthesis of dl-1-O-benzoyl-myo-inositol (16a) General procedure: To a solution of 1 (96 mg, 0.54 mmol), LiCl (400 mg, 9.44 mmol) and triethylamine (225 mg, 2.22 mmol) in DMA (5 mL) cooled at -23 °C was slowly added benzoyl chloride (117 mg, 0.83 mmol), and the mixture was stirred for 2 h at the same temperature and then methanol was added. After 10 min, TMSCl (2 mL) and pyridine (4 mL) were added, the mixture was stirred for 3 h at rt, cooled to 0 °C, and then H2O (0.1 mL) was added. After being stirred for 10 min, the solution was partitioned to AcOEt and H2O layers. The organic solution was washed with H2O (×3), 0.5 N HCl solution, H2O, saturated NaHCO3 solution, H2O, and then brine, dried (MgSO4), filtered and then evaporated. The residue was dissolved in CHCl3 (1 mL) and MeOH (2 mL), and CF3CO2H (one drop) were added. The solution was stirred for 2 h at rt, and all the volatile materials were distilled off under reduced pressure (1.0 mmHg). The residue was subjected to a column chromatography on silica gel (MeOH/CHCl3 1:4) to give crystalline 1-O-benzoate 16a (120 mg, 78%) and 11a (29 mg, 13%). Rf 0.3 (MeOH/CHCl3 1:4); mp 194-195 °C (MeOH/hexane);40 1H NMR (270 MHz, DMSO-d6+D2O) δ 3.07 (1H, t, J=9.7 Hz), 3.30 (1H, t, J=9.7 Hz), 3.42 (1H, t, J=9.7 Hz), 3.94 (1H, t, J=9.7 Hz), 3.94 (1H, br), 4.65 (1H, dd, J=9.7 and 2.4 Hz), 7.49 (2H, t, J=7.4 Hz), 7.62 (1H, t, J=6.2 Hz), 7.99 (2H, d, J=8.4 Hz); 13C NMR (100 MHz, D2O) δ 69.93, 70.44, 70.75, 72.21, 74.10, 74.44, 128.74 (2C), 128.94 (2C), 129.64, 134.05, 167.81; IR (KBr) 3500 (sharp), 3425 (broad), 3330 (broad), 3240 (broad), 1705, 1688 cm-1; LRMS (FAB+, m-nitrobenzyl alcohol) m/z 285 [M+1]; Anal. Calcd for C13H16O7: C, 54.66; H, 5.60. Found: C, 54.93; H, 5.67.

Reference： [1]Watanabe, Yutaka; Uemura, Tsuyoshi; Yamauchi, Satoe; Tomita, Kousei; Saeki, Takafumi; Ishida, Ryousuke; Hayashi, Minoru [Tetrahedron, 2013, vol. 69, # 23, p. 4657 - 4664]

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Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
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Code	Phrase
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Code	Phrase
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P304	IF INHALED:
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P306	IF ON CLOTHING:
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P320
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P321
P322
P330	Rinse mouth.
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P332	IF SKIN irritation occurs:
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P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
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P353	Rinse skin with water/shower.
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P363	Wash contaminated clothing before reuse.
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P371	In case of major fire and large quantities:
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P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
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P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
P402	Store in a dry place.
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P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
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P411 + P235	Keep cool.
Disposal
Code	Phrase
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
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H226	Flammable liquid and vapour
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H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
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H351	Suspected of causing cancer
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H361d	Suspected of damaging the unborn child
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H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 52499-14-6 ] {[proInfo.proName]}

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[ 52499-14-6 ] Synthesis Path-Upstream 1~1

[ 52499-14-6 ] Synthesis Path-Downstream 1~9

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