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[ CAS No. 60924-38-1 ]

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2D
Chemical Structure| 60924-38-1
Chemical Structure| 60924-38-1
Structure of 60924-38-1 *Storage: {[proInfo.prStorage]}

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Product Details of [ 60924-38-1 ]

CAS No. :60924-38-1MDL No. :MFCD13194965
Formula : C23H36O7S Boiling Point : 571.0±50.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :IKVZCNHNKCXZHZ-VIRBKFQOSA-N
M.W :456.59Pubchem ID :71307485
Synonyms :

Computed Properties of [ 60924-38-1 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 60924-38-1 ]

Signal Word:WarningClassN/A
Precautionary Statements:P280-P305+P351+P338UN#:N/A
Hazard Statements:H302Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 60924-38-1 ]

  • Upstream synthesis route of [ 60924-38-1 ]
  • Downstream synthetic route of [ 60924-38-1 ]

[ 60924-38-1 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 124-63-0 ]
  • [ 60924-38-1 ]
YieldReaction ConditionsOperation in experiment
95.6% With triethylamine In dichloromethane at -15 - 1℃; for h; Pleuromutilin (222.Og, 0.59mol) was dissolved in dichloromethane (2.25L) under nitrogen and triethylamine (92mL, 66.45g, 0.66mol) was added at ambient temperature over 15min, during which time a slight exotherm (16.5 to 18.50C) was observed. After stirring for 30min the solution was cooled to -150C over 20min. A solution of methane sulphonyl chloride (52mL, 77.5g, 0.68mol) in dichloromethane (43OmL) was added over 1.28h at -9 to -15°C. The mixture was left to stir in the ice/salt bath at ~ -9°C initially. The mixture was stirred for a total of 1.5h during which time it warmed up to 1°C. Deionized water (1.15L) was added slowly while maintaining the temperature below 12°C. The mixture was stirred for 20 min and the phases separated. The dichloromethane phase (wt = 3.70kg) containing the title compound (267.8g at 100percent yield) was used directly in Step 5a.; Step 1b - Alternative preparation of pleuromutilin-22-mesylatePleuromutilin (69.95g at 90percent purity) and triethylamine (26mL, 18.33g) in dichloromethane (0.55L) were cooled to -1O0C. Methane sulphonyl chloride (14.5mL,20.87g) in dichloromethane (0.12L) was added over 0.5h at -5 to -1O0C. After 0.5h the mixture was warmed to 15-2O0C and water (0.25L) added. The phases were separated and the aqueous phase was further extracted with dichoromethane (0.06L). The combined dichloromethane solution was concentrated by distillation collecting 0.5L. The distillation was continued by slowly adding propan-2-ol (0.3L) and collecting a further 0.3L to reach a solution temperature of 780C. n-Heptane (0.29L) was added slowly whilst maintaining the temperature between 75-8O0C. The solution became turbid with the product crystallizing. The mixture was cooled to O0C and stirred for 1h. The product was filtered off, washed with chilled 2:1 n-heptane/propan-2-ol (0.075L) and dried under vacuum to give the title compound (75.33g, 95.6percent).
90.5% With triethylamine In (methyl)isobutyl ketone at -10 - -5℃; for 1.00 h; Pleuromutilin (20.1g) and triethylamine (6.86g) in methylisobutyl ketone (0.21 L) were cooled to -100C. Methane sulphonyl chloride (7.91 g) in methylisobutyl ketone (0.04L) was added at -5 to -1O0C. After 1 h water (0.12L) was added and the mixture was warmed to 20-220C. The phases were separated and the methylisobutyl ketone phase was washed successively with water (0.09L) and 10percent brine (0.05L). The methylisobutyl ketone solution was concentrated by distillation under reduced pressure to leave a EPO <DP n="9"/>residue of 57.4g. Heptane (0.06L) was added to the residue at 76-780C to crystallize the title compound. Further heptane (0.04L) was added, the mixture was cooled to -5 to -80C and stirred for 1h. The title compound was filtered off, washed with chilled heptane/methylisobutyl ketone (3:1 , 0.028L) and dried at < 4O0C to give 21.94g, 90.5percent yield.
80% With triethylamine In toluene at 5 - 20℃; for 2.00 h; Example 2
Preparation of Pleuromutilin Mesylate
A 3 neck-flask (250 ml) is charged with Pleuromutilin (PLM) (10 g), Toluene (70 ml) and triethyl amine (TEA) (4.6 ml).
The mixture is cooled to 5° C. and a solution of methanesulfonyl chloride (2.5 ml) in toluene (20 ml) is added dropwise.
The reaction mixture is stirred at room temperature overnight.
Pleuromutilin mesylate is obtained in more then 95percent conversion.
The solution is used with no other purification.
Example 5Preparation of Pleuromutilin MesylateA 250 ml round bottom flask was charged with Pleuromutilin (10 g, 0.0263 mol), Et3N (4.2 ml, 0.02895 mol) and Toluene (10 vol, 100 ml). Methane sulfonyl chloride (1 eq, 2 ml, 0.02575 mol) was added at room temperature. The turbid solution became a massive white slurry. The reaction mixture was stirred for 2 hours at room temperature. Water (100 ml) was added to the reaction mixture and the 2 phases were separated. The organic phase was evaporated until dryness and the residue was crystallized in isopropyl alcohol (IPA) (50 ml, 5 vol.) at room temperature over night. The obtained precipitate was filtered under reduced pressure and dried under vacuum at 50° C. overnight to obtain 9.72 g of Pleuromutilin mesylate as a white solid (80percent yield, 100.5percent purity by assay).
78.5% With triethylamine In 2-methylpropyl acetate at 20℃; for 1.50 h; Example 7
Preparation of Pleuromutilin Mesylate
A 250 ml round bottom flask was charged with Pleuromutilin (10 g, 0.0263 mol), Et3N (4.2 ml, 0.02895 mol) and Isobutyl acetate (15 vol, 150 ml (Fluka)).
Methane sulfonyl chloride (1.1 eq, 2.25 ml, 0.03 mol) was added at room temperature.
The solution became a massive white slurry.
The reaction mixture was stirred for 1.5 hours at room temperature and then filtered and washed with Isobutyl acetate (10 ml).
The Isobutyl acetate was evaporated until dryness to give 15.12 g oil.
Cyclohexane (10 vol) was added to the oil and the mixture was stirred at room temperature overnight.
The obtained precipitate was filtered under reduced pressure, washed with cyclohexane (50 ml*2) and dried under vacuum at 50° C. overnight to obtain 10.33 g of Pleuromutilin mesylate as a white precipitate (78.5percent yield).
77% With triethylamine In 4-methyl-2-pentanone at -3 - 25℃; for h; Example 1
Preparation of Pleuromutilin Mesylate
A flask (2 L) was loaded with pleuromutilin (120 g), methyl isobutyl ketone (MIBK) (800 ml) and Et3N (60 ml).
The solution was cooled to -3° C. and a solution of methanesulfonyl chloride (51 ml) in MIBK (150 ml) was added dropwise to the solution while maintaining the temperature between -3° C. and 10° C.
The addition of the methanesulfonyl chloride resulted in the formation of a slurry.
The slurry was heated slowly to 25° C.
The slurry was then extracted with water (500 ml) and the phases were separated.
The organic phase was washed with water (250 ml), washed with brine (130 ml) and dried with Na2SO4.
The organic phase was then evaporated to dryness.
The resulting residue was dissolved in isopropyl alcohol (IPA) (400 ml), the solution was heated to reflux and then cooled to room temperature to precipitate pleuromutilin mesylate.
The precipitated pleuromutilin mesylate was filtered from the solution and dried at 50° C. in a vacuum oven overnight.
Approximately 116 g of pleuromutilin mesylate were obtained.
Example 3Preparation of Pleuromutilin MesylateA 250 ml round bottom flask was charged with Pleuromutilin (10 g, 0.0263 mol), Et3N (4.2 ml, 0.02895 mol) and methyl isobutyl ketone (MIBK) (3 vol, 30 ml). Methane sulfonyl chloride (2 eq, 4 ml, 0.0515 mol) was added at room temperature. The solution became a massive white slurry. The reaction mixture was stirred for 2 hours at room temperature, and then filtered and washed with MIBK (10 ml).n-Hexane (15 vol) was added and the mixture was stirred at room temperature overnight. The obtained precipitate was filtered under reduced pressure and dried under vacuum at 50° C. overnight to obtain 10.33 g of Pleuromutilin mesylate as a white precipitate (86percent yield).; Example 4Preparation of Pleuromutilin MesylateA 250 ml round bottom flask was charged with Pleuromutilin (10 g, 0.0263 mol), Et3N (4.2 ml, 0.02895 mol) and methyl isobutyl ketone (MIBK) (10 vol, 100 ml). Methane sulfonyl chloride (1.1 eq, 2.25 ml, 0.029 mol) was added at room temperature. The solution became a massive white slurry. The reaction mixture was stirred for 1.5 hours at room temperature, and then filtered and washed with MIBK (10 ml.x.2). The filtrate was evaporated to dryness. The residue was crystallized in isopropyl alcohol (IPA) (40 ml, 4 vol) at room temperature overnight. The obtained precipitate was filtered under reduced pressure and dried under vacuum at 50° C. overnight to obtain 9.33 g of Pleuromutilin mesylate as a white solid (77percent yield, 99.3percent purity by assay).
35% With triethylamine In ethyl acetate at 20℃; for 1.50 h; Example 6
Preparation of Pleuromutilin Mesylate
A 250 ml round bottom flask was charged with Pleuromutilin (10 g, 0.0263 mol), Et3N (4.2 ml, 0.02895 mol) and Ethyl acetate (15 vol, 150 ml).
Methane sulfonyl chloride (1.1 eq, 2.25 ml, 0.03 mol) was added at room temperature.
The solution became a massive white slurry.
The reaction mixture was stirred overnight at room temperature, and then filtered and washed with Ethyl acetate (10 ml).
The Ethyl acetate was evaporated until dryness.
Isopropyl alcohol (IPA) (5 vol) was added to the residue and the mixture was stirred at room temperature for 5 hours.
The obtained precipitate was filtered under reduced pressure, washed with IPA (5 ml*2) and dried under vacuum at 50° C. overnight to obtain 5.51 g of Pleuromutilin mesylate as a white precipitate (41.7percent yield).
Example 8Preparation of Pleuromutilin MesylateA 250 ml round bottom flask was charged with Pleuromutilin (10 g, 0.0263 mol), Et3N (7.6 ml, 0.05263 mol) and Ethyl acetate (15 vol, 150 ml). Methane sulfonyl chloride (1.5 eq, 3 ml, 0.0386 mole) was added at room temperature. The solution became a massive white slurry. The reaction mixture was stirred for 1.5 hours at room temperature and then filtered and washed with Ethyl acetate (20 ml.x.2). The Ethyl acetate was evaporated until dryness to give 16 g oil.Isopropyl alcohol (IPA) (5 vol) was added to the residue and the mixture was stirred at room temperature overnight. The obtained precipitate was filtered under reduced pressure, washed with IPA (10 ml.x.2) and dried under vacuum at 50° C. overnight to obtain 4.38 g of Pleuromutilin mesylate as a white precipitate (35percent yield).

Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 12, p. 1927 - 1939
[2] Patent: WO2006/92334, 2006, A1. Location in patent: Page/Page column 7
[3] Patent: WO2006/92334, 2006, A1. Location in patent: Page/Page column 7-8
[4] Patent: US2009/149655, 2009, A1. Location in patent: Page/Page column 3; 4
[5] Patent: US2009/149655, 2009, A1. Location in patent: Page/Page column 3; 4
[6] Patent: US2009/149655, 2009, A1. Location in patent: Page/Page column 3; 4
[7] Patent: US2009/149655, 2009, A1. Location in patent: Page/Page column 3; 4; 5
[8] Patent: US2009/149655, 2009, A1. Location in patent: Page/Page column 3; 5
[9] Patent: US2009/149655, 2009, A1. Location in patent: Page/Page column 3; 5
[10] Patent: WO2010/56855, 2010, A1. Location in patent: Page/Page column 14
[11] Patent: CN104693126, 2017, B. Location in patent: Paragraph 0018; 0019; 0020; 0023; 0024; 0027; 0028
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