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[ CAS No. 60924-38-1 ]

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Cat. No.: {[proInfo.prAm]}
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 :-
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:WarningClass:N/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
  • [ 848130-83-6 ]
  • [ 60924-38-1 ]
  • [ 224452-66-8 ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine In 4-methyl-2-pentanone at 20 - 40℃; for 2 - 24 h; Example 17
Preparation of Retapamulin
A 3 neck-flask (100 ml) was charged with tropine thiol (5-10 mmol), a solvent (5 vol) and a base (2.5 eq).
The solvents and bases are listed in Table 1 below.
Pleuromutilin mesylate (11 mmol) was then added to the flask in portions.
The resulting combination was stirred at room temperature to 40° C. for 2-24 hours until full conversion to Retapamulin was achieved.
Example 18Preparation of RetapamulinIn a 500 ml round bottom flask, tropine thiol (15 g), methyl isobutyl ketone (8 vol) and triethylamine (2.4 eq.) were charged. The mixture was stirred at 40° C. for 15 minutes. Pleuromutilin mesylate (1 eq.) was added. The mixture was stirred as a slurry at 40° C. for 12 hours. Water (7 vol) was added and the pH was adjusted to 8.5 using 4N HCl. The phases were separated. Water (7 vol) was added to the organic phase, the pH was adjusted to 8.2, and the phases separated again. The organic phase was extracted with water (7 vol) and the pH was adjusted to 1.5. After separation, the pH of the aqueous phase was adjusted to 12.5 with 4N NaOH. The mixture was stirred at room temperature for 20 hours. The product was vacuum filtered and washed with water. The collected crystals were dried in a 55° C. vacuum oven to yield 80percent Retapamulin at 99.8percent purity as determined by HPLC.
69.2% at 30℃; for 2 h; Cooling with ice; Green chemistry A solution of (1R, 3s, 5S) -8-methyl-8-azabicyclo [3.2.1] octane-3-thiol (6) obtained in Example 6 was added with pleuromutil mesylate 2(23.44 g, 51.38 mmol, 1 eq.),The mixture was cooled in an ice-water bath (internal temperature <30 ° C.) and 2 mol / L H2SO4 (90 ml, 359.66 mmol, 7 eq.) Was added dropwise thereto and reacted at 30 ° C. for 2 h. After the reaction was completed, the pH was adjusted with 2 mol / L HCl (25 ml, 1 eq.)≈8, EtOH (35 ) was evaporated under reduced pressure, water (280ml) and ethyl acetate (200ml) were added, mixed, separated and separated.The aqueous phase is extracted with ethyl acetate (150 ml + 50 ml).The organic phases were combined, washed with water (35ml), added with 4mol / L HCl (100ml) and stirred for 10min, allowed to stand, layered and separated.The organic phase was added 4mol / L HCl (100ml), stirred for 10min, allowed to stand, layered and separated.The organic phase was added with 4mol / L HCl (40ml), stirred for 10min, allowed to stand, layered and separated.Hydrochloric acid layers were combined and adjusted to pH 8 with 6 mol / L NaOH (200 ml) under ice-water bath and extracted with ethyl acetate (200 ml + 100 ml).The ethyl acetate layers were combined, washed with water (40 ml) and dried over anhydrous Na2SO4. The mixture was suction filtered and the ethyl acetate (40 ° C) was evaporated under reduced pressure to give 21.8 g of an off-white solid.Add EtOH / H2O (1: 1,110ml) heated to dissolve, the temperature was lowered to 50 ° C with stirring seed, cooled to room temperature and stirred (14h), precipitated a large amount of solid, suction filtered.The filter cake was washed with EtOH: H2O (1: 1, 15ml) and baked at 60 ° C for 6h to obtain 18.4g of white solid with a yield of 69.2percent
Reference: [1] Patent: US2009/149655, 2009, A1, . Location in patent: Page/Page column 3; 5; 6
[2] Patent: CN105198873, 2017, B, . Location in patent: Paragraph 0023; 0069; 0070; 0071
[3] Patent: US2009/149655, 2009, A1, . Location in patent: Page/Page column 3; 5; 6
[4] Patent: US2009/149655, 2009, A1, . Location in patent: Page/Page column 3; 5; 6
[5] Patent: US2009/149655, 2009, A1, . Location in patent: Page/Page column 3; 5; 6
[6] Patent: US2009/149655, 2009, A1, . Location in patent: Page/Page column 3; 5; 6
[7] Patent: US2009/149655, 2009, A1, . Location in patent: Page/Page column 3; 5; 6
[8] Patent: US2009/149655, 2009, A1, . Location in patent: Page/Page column 3; 5; 6
[9] Patent: US2009/149655, 2009, A1, . Location in patent: Page/Page column 3; 5; 6
[10] Patent: US2009/149655, 2009, A1, . Location in patent: Page/Page column 3; 5; 6
[11] Patent: US2009/149655, 2009, A1, . Location in patent: Page/Page column 3; 5; 6
[12] Patent: US2009/149655, 2009, A1, . Location in patent: Page/Page column 3; 5; 6
[13] Patent: US2009/149655, 2009, A1, . Location in patent: Page/Page column 3; 5; 6
[14] Patent: US2009/149655, 2009, A1, . Location in patent: Page/Page column 3; 5; 6
[15] Patent: US2009/149655, 2009, A1, . Location in patent: Page/Page column 3; 5; 6
[16] Patent: US2009/149655, 2009, A1, . Location in patent: Page/Page column 3; 5; 6
[17] Patent: US2009/149655, 2009, A1, . Location in patent: Page/Page column 3; 5; 6
[18] Patent: US2009/149655, 2009, A1, . Location in patent: Page/Page column 3; 5; 6
[19] Patent: US2009/149655, 2009, A1, . Location in patent: Page/Page column 3; 5; 6
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