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Product Details of [ 773-64-8 ]

CAS No. :773-64-8 MDL No. :MFCD00007434
Formula : C9H11ClO2S Boiling Point : -
Linear Structure Formula :- InChI Key :PVJZBZSCGJAWNG-UHFFFAOYSA-N
M.W :218.70 Pubchem ID :13046
Synonyms :

Calculated chemistry of [ 773-64-8 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 54.42
TPSA : 42.52 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.33
Log Po/w (XLOGP3) : 3.04
Log Po/w (WLOGP) : 3.62
Log Po/w (MLOGP) : 2.47
Log Po/w (SILICOS-IT) : 2.69
Consensus Log Po/w : 2.83

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.39
Solubility : 0.0898 mg/ml ; 0.000411 mol/l
Class : Soluble
Log S (Ali) : -3.6
Solubility : 0.0551 mg/ml ; 0.000252 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.11
Solubility : 0.0171 mg/ml ; 0.000078 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.8

Safety of [ 773-64-8 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310 UN#:3261
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 773-64-8 ]

* 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 [ 773-64-8 ]
  • Downstream synthetic route of [ 773-64-8 ]

[ 773-64-8 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 108-67-8 ]
  • [ 773-64-8 ]
Reference: [1] Journal of Physical Organic Chemistry, 2018, vol. 31, # 2,
[2] Tetrahedron, 1994, vol. 50, # 16, p. 4775 - 4794
[3] Organic Syntheses, 1997, vol. 74, p. 217 - 217
[4] Journal of the American Chemical Society, 1934, vol. 56, p. 696
[5] Recueil des Travaux Chimiques des Pays-Bas, 1935, vol. 54, p. 544,550
[6] Recueil des Travaux Chimiques des Pays-Bas, 1931, vol. 50, p. 60,69, 70
[7] Journal of the American Chemical Society, 1941, vol. 63, p. 3446
[8] Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 11, p. 2144 - 2146[9] Zhurnal Organicheskoi Khimii, 1987, vol. 23, # 11, p. 2429 - 2431
  • 2
  • [ 6148-75-0 ]
  • [ 773-64-8 ]
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 7, p. 1499 - 1501
  • 3
  • [ 3453-83-6 ]
  • [ 773-64-8 ]
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 7, p. 1499 - 1501
  • 4
  • [ 576-83-0 ]
  • [ 773-64-8 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 12, p. 3170 - 3173
  • 5
  • [ 7719-09-7 ]
  • [ 3453-83-6 ]
  • [ 773-64-8 ]
  • [ 1939-97-5 ]
Reference: [1] Monatshefte fuer Chemie, 1913, vol. 34, p. 576
  • 6
  • [ 773-64-8 ]
  • [ 16182-15-3 ]
Reference: [1] Organic Syntheses, 1997, vol. 74, p. 217 - 217
[2] Antimicrobial Agents and Chemotherapy, 2002, vol. 46, # 8, p. 2450 - 2457
[3] Chemistry - A European Journal, 2012, vol. 18, # 6, p. 1582 - 1585
[4] ACS Combinatorial Science, 2015, vol. 17, # 11, p. 658 - 662
[5] Chemistry - An Asian Journal, 2016, vol. 11, # 4, p. 478 - 481
[6] Medicinal Chemistry Research, 2016, vol. 25, # 7, p. 1425 - 1432
[7] European Journal of Organic Chemistry, 2017, vol. 2017, # 24, p. 3512 - 3515
[8] Research on Chemical Intermediates, 2017, vol. 43, # 11, p. 6601 - 6616
[9] Organic Letters, 2018, vol. 20, # 7, p. 1703 - 1706
  • 7
  • [ 773-64-8 ]
  • [ 10576-12-2 ]
  • [ 38202-27-6 ]
YieldReaction ConditionsOperation in experiment
94% With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; A solution of ethyl N-hydroxyacetimidate (2.00 g, 19.4 mmol), N,N-diisopropylethylamine (3.01 g, 23.3 mmol) and 4-dimethylaminopyridine (240 mg, 1.96 mmol) in anhydrous dichloromethane (30 mL) was cooled to 0 °C. To this cold solution 2,4,6-trimethylbenzene-1-sulfonyl chloride (4.66 g, 21.3 mmol) was added slowly, warmed to room temperature and stirred for 1 hour. The reaction was quenched with the addition of water (40 mL) and this mixture was extracted with dichloromethane (30 mL, 3 times). The combined dichloromethane layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The crude obtained was purified by silica flash column chromatography with 5percent ethyl acetate in hexanes as the eluent to obtain 9 as white solid (5.19 g, 94percent). 1H NMR (400 MHz, CDCl3) δ 6.94 (s, 2H), 3.88 (q, J = 7.1 Hz, 2H), 2.62 (s, 6H), 2.28 (s, 3H), 2.00 (s, 3H), 1.15 (t, J = 7.1 Hz, 3H). 13C NMR (101 MHz, CDCl3) δ 169.1, 143.3, 140.6, 131.5, 130.3, 63.6, 22.8, 21.0, 14.8, 13.9; HRMS (ESI/TOF) m/z calcd for C13H20NO4S+ [M + H]+ 286.1108, found 286.1115.
92% With triethylamine In N,N-dimethyl-formamide at 0℃; Ethyl N-hydroxyacetimidate (10.3 g, 47 mmol, 1.1 eq) and triethylamine (25.5 ml, 94 mmol, 2 eq) were dissolved in DMF (40 ml, 2 vol) and the mixture cooled to 0 °C. O-mesitylene chloride (20 g, 47 mmol, 1 eq) was then added portionwise and the mixture stirred at 0 °C for 45 minutes. The above solution was poured into ice water, and solid obtained was filtered and washed with water. Yield : 23 g (92 percent). 1HNMR (400MHz, DMSO-d6): 5 1.16 (t, 3H), 2.03 (s, 3H), 2.31 (s, 3H), 2.64 (s, 6H), 3.89 (q, 2H), 6.96 (s, 2H).
87% With sodium hydroxide In ethanol at 15 - 25℃; for 2 h; Into a 500mL reaction flask added ethyl acetohydroxamate (71g, 0.5mol, 1.0eq) and ethanol (284mL, 4P) to form into an ethanol solution of ethyl acetohydroxanoate, into ethyl acetohydroxanoate ethanol solution added sodium hydroxide (24g, 0.6mol, 1.2eq), added the drops of 2,4,6-trimethylbenzenesulfonyl chloride (120.3g, 0.55mol, 1. 1eq), magnetic stirring speeds up the reaction, the reaction temperature is controlled between 15-25 ° C, after the addition is completed, the temperature is maintained between 15-25 ° C for 2 hours, reaction solution added into water (284mL, 4P), the precipitated solid is suction filtered, and then obtained filter cake is washed with ethanol, obtained solid is dried and then obtained 244g of ethyl O-(2,4,6-trimethylbenzenesulfonyl)acetohydroxamate, yield is 87percent
Reference: [1] RSC Advances, 2018, vol. 8, # 25, p. 13755 - 13763
[2] Synthetic Communications, 2018, vol. 48, # 6, p. 626 - 631
[3] Patent: WO2011/112186, 2011, A1, . Location in patent: Page/Page column 202
[4] Patent: CN108530315, 2018, A, . Location in patent: Paragraph 0100-0102
[5] Journal of Heterocyclic Chemistry, 2007, vol. 44, # 6, p. 1383 - 1387
[6] Organic Letters, 2017, vol. 19, # 19, p. 5490 - 5493
[7] Archiv der Pharmazie, 2006, vol. 339, # 5, p. 262 - 266
[8] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 934 - 945
[9] The Journal of organic chemistry, 1973, vol. 38, # 6, p. 1239 - 1241
[10] Patent: WO2008/9487, 2008, A1, . Location in patent: Page/Page column 68
[11] Journal of the American Chemical Society, 2008, vol. 130, # 30, p. 9642 - 9643
[12] Journal of Heterocyclic Chemistry, 2009, vol. 46, # 2, p. 309 - 316
[13] Angewandte Chemie - International Edition, 2011, vol. 50, # 18, p. 4127 - 4132
[14] Patent: US2012/178913, 2012, A1, . Location in patent: Page/Page column 8
  • 8
  • [ 773-64-8 ]
  • [ 36016-38-3 ]
  • [ 36016-39-4 ]
YieldReaction ConditionsOperation in experiment
96% With triethylamine In tetrahydrofuran at 0℃; for 1.16667 h; Inert atmosphere MC825 scaffold Step 1-IS08115-029 0-(2,2-dimethylpropano l)-A/-f(mesitylsulfonyl)oxy1hvdroxylamine Procedure: To a solution of 2-mestylenesulphonylchloride (5 g, 22.8 mmol) in dry tetrahydrofuran (75 ml_), N-boc-hydroxylamine (3.34 g, 25.1 mmol) is added and cooled to 0°C. Triethylamine (3.8 mL, 27.4 mmol) is added slowly over 10 min. The reaction mixture is stirred for 1 h at 0°C. The reaction mixture is concentrated and the residue is taken in dichloromethane (75 mL) and washed with water (2 * 75mL), an aqueous solution of NaHC03 (10percent, 75 mL) and dried over MgSO4and concentrated to get the product. Yield: 96 percent (7 g, off white solid). 1H NMR (400 MHz, DMSO-d6): δ [ppm] 11.16 (s, 1H), 7.12 (s, 2H), 2.49 (s, 6H), 2.28 (s, 3H), 1.23 (s, 9H).
93% With triethylamine In tert-butyl methyl ether at 0 - 20℃; for 2 h; To a stuffed solution of 2,4,6-trimethylbenzene-1-sulfonyl chloride (4.80 g, 22.01mmol) and tert-butyl hydroxycarbamate (3.22 g, 24.21 mmol) in MTBE (45 mL) wasadded triethylamine (3.40 mL, 24.21 mmol) slowly at 0°C. The reaction mixture was stirred at room temperature for 2 h. The resulting solid was filtered and washed with MTBE (100 mL) and hexane. The combined organic layer was dried over sodium sulphate, then concentrated in vacuo, to give the title compound (6.44 g, 93 percent). oH (400MHz, CDC13) 7.57 (s, 1H), 6.99 (s, 2H), 2.68 (s, 6H), 2.32 (s, 3H), 1.32 (s, 9H).
89% With triethylamine In tert-butyl methyl ether at 0℃; for 0.5 h; To a 0 °C solutionof 2,4,6-trimethylbenzene-1-sulfonyl chloride (10.0 g, 45.72 mmol) and tert-butyl hydroxycarbamate (6.088 g, 45.72 mmol) in MTBE (100 mL) was added TEA (14.46 mL, 48.01 mmol) drop-wise while stirring. The resulting suspension was stirred at 0 °C for an additional 30 mm and then warmed to ambient temperature. The reaction was then diluted with water (100 mL), adjusted to pH 4 with 1 N HC1(aq). The organic layer was dried (Na2504), filtered and concentrated to yield the title compound initially as a yellowish oil, which upon drying overnight under high vacuum became a white solid (12.89 g, 89percent yield). ‘H NMR (CDC13) 7.66 (br s, 1H), 6.98 (s, 2H), 2.67 (s, 6H), 2.32 (s, 3H), 1.31 (s, 9H).
89% With triethylamine In tert-butyl methyl ether at 0℃; To a 0 °C solution of 2,4,6-trimethylbenzene-1-sulfonyl chloride (10.0 g, 45.72 mmol) and tert-butyl hydroxycarbamate (6.088 g, 45.72 mmol) in MTBE (100 mL) was added TEA (14.46 mL, 48.01 mmol) dropwise while stirring. The resulting suspension was stirred at 0 °C for an additional 30 mm and then warmed to ambient temperature. The reaction was then diluted with water (100 mL), adjusted to pH 4 with 1 N HC1(aq). The organic layer was dried (Na2504), filtered and concentrated to yield the title compound initially as a yellowish oil, which upon drying overnight under high vacuum became a white solid (12.89 g, 89percent yield). ‘H NIVIR (CDC13) 7.66 (br s, 1H), 6.98 (s, 2H), 2.67 (s, 6H), 2.32 (s, 3H), 1.31 (s, 9H).
89% With triethylamine In tert-butyl methyl ether at 0℃; for 0.5 h; Preparation of tert-butyl mesitylsulfonyl)oxycarbamate. To a 0 °C solution of 2,4,6-trimethylbenzene-l-sulfonyl chloride (10.0 g, 45.72 mmol) and tert-butyl hydroxycarbamate (6.088 g, 45.72 mmol) in MTBE (100 mL) was added TEA (14.46 mL, 48.01 mmol) drop-wise while stirring. The resulting suspension was stirred at 0 °C for an additional 30 min and then warmed to ambient temperature. The reaction was then diluted with water (100 mL), adjusted to pH 4 with 1 N HCl(aq). The organic layer was dried (Na2S04), filtered and concentrated to yield the title compound initially as a yellowish oil, which upon drying overnight under high vacuum became a white solid (12.89 g, 89percent yield). NMR (CDCh) δ 7.66 (br s, 1H), 6.98 (s, 2H), 2.67 (s, 6H), 2.32 (s, 3H), 1.31 (s, 9H).
89% With triethylamine In tert-butyl methyl ether at 0℃; for 0.5 h; To a 0 °C solution of 2,4,6-trimethylbenzene-l-sulfonyl chloride (10.0 g, 45.72 mmol) and tert-butyl hydroxycarbamate (6.088 g, 45.72 mmol) in MTBE (100 mL) was added TEA (14.46 mL, 48.01 mmol) drop-wise while stirring. The resulting suspension was stirred at 0 °C for an additional 30 min and then warmed to ambient temperature. The reaction was diluted with water (100 mL), adjusted to pH 4 with 1 N HCl(aq). The organic layer was dried (Na2S04), filtered and concentrated to yield the title compound initially as a yellowish oil, which upon drying overnight under high vacuum became a white solid (12.89 g, 89percent yield). MR (CDCh) δ 7.66 (br s, 1H), 6.98 (s, 2H), 2.67 (s, 6H), 2.32 (s, 3H), 1.31 (s, 9H).
88% With triethylamine In tert-butyl methyl ether at 0 - 3℃; Industrial scale To a stirred solution of 2,4,6-trimethylbenzene-1-sulfonyl chloride (5.5 Kg, 25.14 mol) in MTBE (55 L) is added tert-butyl hydroxycarbamate (4 Kg, 30.17 mol) and cooledto 0 °C. Triethylamine (3.05 Kg, 30.17 mol) is added to the reaction mixture over a period of 1 hour and the reaction mixture is stirred at 0 °C for 2 hours. The reactionmixture is filtered and washed with MTBE (2x5 L). The filtrate is concentrated to a volume of 12 L and n-hexane (6 L) is added and the mixture is redistilled up to a volume of 12 L. To the crude compound 5percent solution of MTBE in n-hexane (60 L) is added andthe mixture is stirred for 2 hours. The reaction mixture is filtered to give the first crop as an off white solid compound (6.13 Kg). The filtrate is concentrated to dryness and 5percentsolution of MTBE in n-hexane (10 L) is added. The reaction mixture is stirred for 30 minutes and filtered to give a second crop of the title compound (0.86 Kg) which is combined with the first crop to give the title compound (6.99 g, 88percent).
88% With triethylamine In tert-butyl methyl ether at 0℃; for 3 h; Large scale To a stirred solution of 2,4,6-trimethylbenzene-l-sulfonyl chloride (5.5 Kg, 25.14 mol) in MTBE (55 L) is added tert-butyl hydroxycarbamate (4 Kg, 30.17 mol) and cooled to 0° C. Triethylamine (3.05 Kg, 30.17 mol) is added to the reaction mixture over a period of 1 hour and the reaction mixture is stirred at 0° C. for 2 hours.
The reaction mixture is filtered and washed with MTBE (2*5 L).
The filtrate is concentrated to a volume of 12 L and n-hexane (6 L) is added and the mixture is redistilled up to a volume of 12 L.
To the crude compound 5percent solution of MTBE in n-hexane (60 L) is added and the mixture is stirred for 2 hours.
The reaction mixture is filtered to give the first crop as an off white solid compound (6.13 Kg).
The filtrate is concentrated to dryness and 5percent solution of MTBE in n-hexane (10 L) is added.
The reaction mixture is stirred for 30 minutes and filtered to give a second crop of the title compound (0.86 Kg) which is combined with the first crop to give the title compound (6.99 g, 88percent).
87% With triethylamine In diethyl ether at 0 - 20℃; Inert atmosphere Step 6: tert-butyl mesitylsulfonyloxycarbamate To a solution of 2,4,6-trimethylbenzene-1 -sulfonyl chloride (120 g, 0.55 mol, Beiou) and ferf-butyl hydroxycarbamate (73 g, 0.55 mol, Beiou) in Et20 (1 L) was added TEA (58.3 g, 0.57 mol) drop wise at 0 °C under nitrogen atmosphere. Then, the reaction mixture was stirred at rt for overnight. The mixture was filtered and organic layer was concentrated, the crude product was washed with PE (0.5 L) to afford ferf-butyl mesitylsulfonyloxycarbamate (151 .5 g, 0.48mol, 87 percent yield) as a white solid.
76.3% With triethylamine In diethyl ether at 0℃; for 0.5 h; [00240] To a mixture of 2,4,6-trimethylbenzenesulfonyl chloride (100 g, 457 mmol) and tert-butyl hydroxycarbamate (60.9 g, 457 mmol) in diethyl ether (1000 mL) was added TEA (46.3 g, 24.9 mmol) at 0°C. The reaction mixture was allowed to stir at 0°C for 30 mm. The reaction mixture was filtered and washed with MTBE (250 mL). The solution was concentrated at 20°C at 150mm Hg to remove the diethyl ether. The reaction mixture was then diluted with petroleum ether (1500 niL) and allowed to stir for 5 mm. The reaction mixture was filtered and washed with petroleum ether (300 mL) to provide tertbutyl [(mesitylsulfonyl)oxy]carbamate (110 g, 76.3percent). 1H NEVER (400 JVEFIz, DMSO-d6) 6 11.19 (s, 1H), 7.14 (s, 2H), 2.54 (s, 6H), 2.30 (s, 3H), 1.25 (s, 9H).
76.3% With triethylamine In diethyl ether at 0℃; for 0.5 h; Step 1:
tert-butyl [(mesitylsulfonyl)oxy]carbamate
To a mixture of 2,4,6-trimethylbenzenesulfonyl chloride (100 g, 457 mmol) and tert-butyl hydroxycarbamate (60.9 g, 457 mmol) in diethyl ether (1000 mL) was added TEA (46.3 g, 24.9 mmol) at 0° C.
The reaction mixture was allowed to stir at 0° C. for 30 min.
The reaction mixture was filtered and washed with MTBE (250 mL).
The solution was concentrated at 20° C. at 150 mm Hg to remove the diethyl ether.
The reaction mixture was then diluted with petroleum ether (1500 mL) and allowed to stir for 5 min.
The reaction mixture was filtered and washed with petroleum ether (300 mL) to provide tert-butyl [(mesitylsulfonyl)oxy]carbamate (110 g, 76.3percent).
1H NMR (400 MHz, DMSO-d6) δ 11.19 (s, 1H), 7.14 (s, 2H), 2.54 (s, 6H), 2.30 (s, 3H), 1.25 (s, 9H).
73% With triethylamine In tetrahydrofuran at 0℃; for 1.25 h; Inert atmosphere N-(tert.-Butoxycarbon l)-0-(mesitylsulfonyl)-hydroxylamineTo a solution of 2-mesitylene sulphonyl chloride (2.0 g, 9.14 mmol) in dry THF (50 ml_), was added N-Boc-hydroxylamine (1.21 g, 9.14 mmol) and cooled to 0 C under N2 atmosphere. The reaction mixture was stirred for 5 minutes. To this mixture triethylamine (1.1 g, 11 mmol) was added slowly over 10 minutes. The reaction mixture was stirred for 1 hour at 0 C and upon completion, the solvent removed in vacuo. The residue was redissolved in dichloromethane (50 ml_) and washed with water (2 x 50 mL), 10percent aqueous NaHCO3 (50 ml_) and dried overMgS04. It was then concentrated under reduced pressure at room temperature to get the product as an off white solid; (2.1 g, 73percent). TLC: pet ether / ethyl acetate (8/2) Rf- 0.4. 1H NMR (DMSO-d6; 400 MHz): δ 11.16 (s, 1 H), 7.12 (s, 2H), 2.49 (s, 6H), 2.28 (s, 3H), 1.23 (s, 9H).
73%
Stage #1: at 0℃; for 0.0833333 h; Inert atmosphere
Stage #2: With triethylamine In tetrahydrofuran at 0℃; for 1.16667 h; Inert atmosphere
8.1 N-(tert-butoxy carbonyl)-0-(mesit lsulfonyl)-hydroxylamine To a solution of 2-mesitylene sulphonyl chloride (2.0 g, 0.00914 mol) in dry THF (50 mL) is added N-Boc-hydroxylamine (1.21 g, 0.00914 mol) and cooled to 0°C under N2 atmosphere. The reaction mixture is stirred for 5 minutes. To this mixture triethylamine (1.1 g, 0.011 mol) is added slowly over 10 minutes. The reaction mixture is stirred for 1 hour 0°C and then the solvent is removed in vacuo. The residue is dissolved in dichloromethane (50 mL) and washed with water (2 x 50 mL), 10percent aqueous NaHC03 (50 ml) and dried over MgS04. It is then concentrated under reduced pressure at room temperature to get the product as an off white solid. (2.1 g, 73percent); TLC: Pet ether / Ethyl acetate (8/2) Rf- 0.4; 1H NMR (DMSO-d6; 400 MHz): δ [ppm] 11.16 (s, 1H), 7.12 (s, 2H), 2.49 (s, 6H), 2.28 (s, 3H), 1.23 (s, 9H).
72% With triethylamine In diethyl ether at 20℃; (a)
O-(Mesitylsulfonyphydroxylamine
To a solution of 2,4,6-trimethylbenzene-1-sulfonyl chloride (30 g, 0.148 mol) and tert-butyl hydroxycarbamate (18 g, 0.148 mol) in Et2O (500 mL) was added Et3N (15 g, 0.148 mol) dropwise over 1 h.
The reaction mixture was stirred at room temperature for 4 h, then filtered.
The filtrate was concentrated.
The product was purified by silica gel column chromatography (5percent v/v EtOAc in PE) to give tert-butyl mesitylsulfonyloxycarbamate as a white solid (31 g, yield 72percent). ESI MS: m/z 338 [M+Na]+.
64% With triethylamine In hexane; benzene 1st step:
Production of t-butyl N-(mesitylenesulphonyloxy)carbamate (Z40) of formula: STR52 with t-Bu=tert-butyl
1 equivalent of triethylamine (3.5 ml-0.025 mol) is added dropwise to 1 equivalent of mesitylenesulphonyl chloride (5.45 g-0.025 mol) and 1 equivalent of t-butyl N-hydroxycarbamate (3.32 g-0.025 mol) dissolved in anhydrous ether (100 ml) at 0° C.
During the reaction, a precipitate of triethylamine hydrochloride gradually forms.
After 0.5 h of stirring at 0° C., this precipitate is filtered off and washed copiously with ether.
The medium is concentrated under vacuum.
5.01 g of pale yellow residue are obtained, which product is recrystallized twice in a minimum amount of hot benzene (8 ml) and of hexane (30 ml).
The yield is 64percent.
The molecular mass is:
M=315.39

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[2] Patent: WO2013/124026, 2013, A1, . Location in patent: Page/Page column 80; 81
[3] Patent: WO2015/86502, 2015, A1, . Location in patent: Page/Page column 81
[4] Patent: WO2017/11776, 2017, A1, . Location in patent: Paragraph 00687; 00688; 00689
[5] Patent: WO2018/71447, 2018, A1, . Location in patent: Paragraph 00802; 00803
[6] Patent: WO2018/71454, 2018, A1, . Location in patent: Paragraph 00929; 00932
[7] Patent: WO2018/136661, 2018, A1, . Location in patent: Paragraph 00882
[8] Patent: WO2015/105779, 2015, A1, . Location in patent: Page/Page column 14
[9] Patent: US2016/333005, 2016, A1, . Location in patent: Paragraph 0052-0053
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[12] Patent: US2015/225422, 2015, A1, . Location in patent: Paragraph 0328-0329
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  • 9
  • [ 773-64-8 ]
  • [ 58042-39-0 ]
YieldReaction ConditionsOperation in experiment
74% With dmap; hydroxylamine hydrochloride In pyridine at 20℃; for 0.0833333 h; Cooling with ice General procedure: To a mixture of hydroxylamine hydrochloride (2 equiv.) and DMAP (2 equiv.) in pyridine (20 mL) was added a portion of arylsulfonyl chloride (1 equiv.) on an ice-bath. Then, the mixture was stirred for 5 min at room temperature. The resulting suspension was poured into AcOEt (100 mL) and 1 N HCl aq. (100 mL). The AcOEt layer was separated, washed with brine (100 mL), dried over Na2SO4, filtered and concentrated. The crude product was purified by flash column chromatography under one of the gradient conditions indicated below, and recrystallized from Et2O/n-hexane to give N-hydroxyarylsulfonamide derivatives.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 8, p. 2340 - 2343
  • 10
  • [ 773-64-8 ]
  • [ 24807-55-4 ]
  • [ 74257-00-4 ]
YieldReaction ConditionsOperation in experiment
48% With triethylamine In 1,4-dioxane for 1.5 h; Cooling with ice An oven dried 1.0 l round-bottomedflask containing a magnetic stir bar was equipped with a Claisen adapter. 3-Nitro-1,2,4-triazole (19.5 g, 0.171 mol), dry dioxane (200 ml) and triethylamine (1.0 equiv., 17.3 g,0.171 mol) was transferred to the reaction flask and the solution was cooled in an ice-bathwith magnetic stirring.47 The Claisen adapter was fitted with a 200 ml pressure-equalizingaddition funnel, containing a dioxane solution (150 ml) of mesitylenesulfonyl chloride(37.4 g, 0.171 mol). The solution of mesitylenesulfonyl chloride was added dropwise overa period of approx. 0.5 h and the final suspension was stirred for an additional 1 h andthen warmed to rt. After removal of the precipitated Et3N·HCl by filtration, the filtratewas concentrated in vacuo to give a yellow solid, which was dissolved in dichloromethane(150 ml) and the solution was washed with water (150 ml).48 The organic layer was driedover anhydrous Na2SO4 and evaporated in vacuo to give a yellow solid. Recrystallizationfrom boiling toluene (20–30 ml) followed by washing with ice-cold toluene and dryingovernight at 1.9 mmHg, provided 24–25 g (46percent–48percent) of the title compound as light yellow solid,49 mp. 131C–133C (lit.37 130C–132C). Rf = 0.23 (20percent hexane in CH2Cl2, UV);1H NMR (300 MHz, CDCl3): δ 8.84 (s, 1H), 7.07 (s, 2H), 2.69 (s, 6H), 2.34 (s, 3H);13C NMR (75 MHz, CDCl3): δ 162.9, 147.5, 145.2, 142.5, 133.0, 127.9, 23.2, 21.3; IR(solid): 3126, 2983, 2947, 1597.Anal. Calcd. for C11H12N4O4S: C, 44.59; H, 4.08; N, 18.91. Found: C, 44.69; H,3.88; N, 18.72. The purity of the product (96percent) established by RP-HPLC, tR = 8.41 min(254 nm).
Reference: [1] Organic Preparations and Procedures International, 2014, vol. 46, # 3, p. 267 - 271
[2] Tetrahedron Letters, 1986, vol. 27, # 45, p. 5529 - 5532
  • 11
  • [ 773-64-8 ]
  • [ 137280-49-0 ]
Reference: [1] Journal of Organic Chemistry, 1999, vol. 64, # 15, p. 5472 - 5478
  • 12
  • [ 625-82-1 ]
  • [ 773-64-8 ]
  • [ 885434-70-8 ]
YieldReaction ConditionsOperation in experiment
58% With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 16 h; To a solution of 2,4-dimethyl-lH-pyrrole (24 mg, 0.25 mmol) and mesitylsulfonyl chloride (218 mg, 1.0 mmol) in 5 mL of THF was added 60percent NaH (40 mg, 1.0 mmol) at 0 °C. The resulting mixture was stirred at r.t. for 16 h. The solution was diluted with EtOAc (50 mL), washed with 1 N HC1 (aq.) (10 mL) and brine (10 mL). The organic layer was dried over anhydrous Na2S04 and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hexane/EtOAc = 10/1) to give the desired product as a pale red solid (40 mg, 58percent). H NMR (600 MHz, CDC13) δ 7.01 (s, 1H), 6.95 (s, 2H), 5.77 (s, 1H), 2.49 (s, 6H), 2.31 (s, 3H), 2.00 (s, 3H), 1.99 (s, 3H). 13C NMR (150 MHz, CDCI3) δ 143.8, 140.2, 133.8, 132.2, 130.2, 119.7, 119.2, 114.5, 23.4, 21.1, 12.6, 11.8.
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 3, p. 952 - 962
[2] Patent: WO2013/119931, 2013, A1, . Location in patent: Paragraph 0201
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