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[ CAS No. 42854-62-6 ]

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2D
Chemical Structure| 42854-62-6
Chemical Structure| 42854-62-6
Structure of 42854-62-6 *Storage: {[proInfo.prStorage]}

Quality Control of [ 42854-62-6 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 42854-62-6 ]

SDS

Product Details of [ 42854-62-6 ]

CAS No. :42854-62-6MDL No. :MFCD00066143
Formula :C17H21NO5SBoiling Point :256.5°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :351.42Pubchem ID :2802424
Synonyms :

Computed Properties of [ 42854-62-6 ]

TPSA : 115 H-Bond Acceptor Count : 6
XLogP3 : - H-Bond Donor Count : 2
SP3 : 0.24 Rotatable Bond Count : 5

Safety of [ 42854-62-6 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305 P351 P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 42854-62-6 ]

  • Upstream synthesis route of [ 42854-62-6 ]
  • Downstream synthetic route of [ 42854-62-6 ]

[ 42854-62-6 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 56-41-7 ]
  • [ 104-15-4 ]
  • [ 100-51-6 ]
  • [ 42854-62-6 ]
YieldReaction ConditionsOperation in experiment
98.6% at 50 - 62℃; for 5.50 h; Into a 300 mL separable flask equipped with a thermometer, stirring apparatus and Dean Stark apparatus was charged 5.00 g (56.12 mmol) of L-alanine, 41.03 g (379.42 mmol) of benzyl alcohol and 12.81 g (67. 34 mmol) of p-toluenesulfonic acid, and mixed, then, the pressure was reduced from 101.3 kPa to 2.0 kPa. The reaction solution was heated, then, water started to be distilled at the inner temperature around 50°C, and the mixture was heated up to 62°C over a period of 2 hours. Under the same pressure and the same temperature, the mixture was stirred for 3.5 hours. The reaction solution was cooled down to 50°C, and 111.66 g of tert-butyl methyl ether was dropped over a period of 30 minutes, then, about 0.005 g (0.01 mmol) of p-toluenesulfonate of L-alanine benzyl ester was added. The mixture was stirred at 50°C for 30 minutes, then, 55.83 g of tert-butyl methyl ether was dropped over a period of 1 hour. The mixture was stirred at 50°C for 1 hour, then, cooled from 50°C to 0°C over a period of 5 hours, and the mixture was stirred at 0°C overnight. The mixture was subjected to a filtration treatment, and the resultant crystal was washed three times with 15.00 g of tert-butyl methyl ether of 0°C. After drying, 18.26 g of p-toluenesulfonate of L-alanine benzyl ester was obtained. The yield against L-alanine was 98.6percent. The optical purity of the p-toluenesulfonate of L-alanine benzyl ester was 99.9percent e.e. or more.
92% for 4.00 h; Dean-Stark; Reflux General procedure: The esterifications were carried out on L amino acids withthe exception of phenylglycine, the D enantiomer of whichwas used. A mixture of amino acid (0.05 mol), p-toluenesulfonicacid (0.06 mol), benzyl alcohol (0.25 mol) andcyclohexane (30 mL) was refluxed for 4 h using a Dean-Stark apparatus to separate water that was azeotroped outas it formed. The reaction mixture was cooled to roomtemperature and ethyl acetate (80 mL) was added. Afterstirring for 1 h, the precipitate was collected by filtrationand dried to give the corresponding benzyl ester p-toluenesulfonateas a white solid. According to this procedure,the amino acids 1–6 were converted into the correspondingbenzyl ester p-toluenesulfonates 1a–6a. The benzylationof 7 was accomplished in the same manner but in thepresence of more p-toluenesulfonic acid (0.11 mol) to givethe di-p-toluenesulfonate 7a as a white solid. The p-toluenesulfonate8a separated at the end of the reaction as anoil; instead of adding ethyl acetate, the supernatant wasremoved, the oily phase was washed with cyclohexane andthen poured into dichloromethane/aqueous Na2CO3. Afterremoving the water layer and evaporating dichloromethane,the residue was treated with hydrochloric methanol to give the corresponding hydrochloride as a white solid. Thebenzylation of 9 was prolonged over night and, at the endof the reaction, 9a separated as an oil, which was pouredinto dichloromethane/water. After removing the organiclayer, the water phase was made alkaline with NaHCO3 andextracted with ethyl acetate. The organic extract was concentratedto a small volume and a slight excess of p-toluenesulfonicacid was added to precipitate 9a as a white crystallinesolid.
72% Dean-Stark; Reflux To a solution of L-alanine (Scheme 2, compound 1-D) (1151.2 mg, 12.9 mmol, 1.00 eq) in 51 mL of toluene, were added (i) 23 mL of BnOH; and (ii) 2457.6 g of APTS.H2O (14.2 mmol, 1.10 eq). Overcoming a Dean-Stark assembly and a condenser, the mixture was stirred at reflux overnight. After completion of the reaction, the mixture was concentrated in vacuo, dissolved in EtOAc (20 mL) and extracted with 1M HCl (3×20 mL). The combined extracts were washed with ether (4×20 mL), adjusted to pH 8-9 with NaHCO3 and extracted with EtOAc (4×20 mL). The combined EtOAc extracts were dried (MgSO4), filtered through fritted glass and concentrated in vacuo. The residue was crystallized in a solution of APTS.H2O (2457.6 mg, mmol, 1 eq) in 20 mL of diethyl ether to give intermediate compound 1-E (Scheme 2) as a white solid (3260.0 mg, (72percent; MS (ES) m/z 180.1 (MH)+).
Reference: [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 2, p. 339 - 345
[2] Patent: EP2062873, 2009, A1. Location in patent: Page/Page column 6
[3] Amino Acids, 2017, vol. 49, # 5, p. 965 - 974
[4] Patent: US2016/97052, 2016, A1. Location in patent: Paragraph 0308
[5] Journal of Antibiotics, 1998, vol. 51, # 8, p. 786 - 794
[6] Journal of Medicinal Chemistry, 2006, vol. 49, # 24, p. 7215 - 7226
  • 2
  • [ 17831-01-5 ]
  • [ 104-15-4 ]
  • [ 42854-62-6 ]
Reference: [1] Letters in Organic Chemistry, 2010, vol. 7, # 1, p. 39 - 44
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