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Chemical Structure| 871224-68-9 Chemical Structure| 871224-68-9

Structure of 871224-68-9

Chemical Structure| 871224-68-9

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Product Details of [ 871224-68-9 ]

CAS No. :871224-68-9
Formula : C16H17NO4S
M.W : 319.38
SMILES Code : O=S(C1=CC=C(C)C=C1)(O[C@@H](C2=CC=CC=C2)C(NC)=O)=O
MDL No. :MFCD11113021

Safety of [ 871224-68-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 871224-68-9 ]

* 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.

  • Downstream synthetic route of [ 871224-68-9 ]

[ 871224-68-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 871224-68-9 ]
  • [ 1169801-28-8 ]
  • [ 913358-93-7 ]
YieldReaction ConditionsOperation in experiment
Synthesis of (2/?)-2-{(7S)-6,7-dimethoxy-1-[2-(4-trifluoromethyl-phenyl)-ethyl]-3,4- dihydro-1H-isoquinolin-2-yl}-Lambda/-methyl-2-phenyl-acetamide hydrochloride(compound I hydrochloride); 1. To a suspension of compound 7*CH3COOH in MIBK is added sodium hydroxide solution (20%) and stirred at RT until the precipitate is dissolved. After phase separation, the organic layer is washed with water. After removal of the water from the organic phase by azeotropic distillation, the solution is diluted with MIBK to a concentration of 9 - 16%.2. To the solution of the compound 7 in MIBK are added 1.2 eq. of the compound 6, 1.1 eq. caustic soda and 1.1 eq. potassium carbonate and heated to 70-90 0C. Water is added and the mixture is heated at the same temperature for 0.5 to 3 hours and then cooled to RT. Alternatively, after full conversion the solution is cooled to RT and water is added. Phase separation is followed by a second washing of the organic phase with water and again phase separation.3. To the organic phase of step 2 is added 1 eq. aqueous hydrochloric acid and then the water removed by azeotropic distillation in vacuo.Then, either:? The precipitate is dissolved by addition of 2-propanol at 75 0C. Concentration of the solution leads to crystallisation and the suspension is then cooled to RT. To ensure complete crystallisation, the suspension is aged at RT, then filtered and washed with a MIBK - 2-propanol mixture.or:The compound I *HCI is obtained by crystallization from the organic phase of step 2 (MIBK) containing an adjusted amount of residual water (0.4 - 1.5%, e.g. 0.7%) without using 2-propanol at a temperature of above 400C (e.g. about 65C) using seeding crystals.The product is isolated e.g. on an inverting bag centrifuge and dried in vacuo at 500C.
  • 2
  • [ 1296659-30-7 ]
  • [ 871224-68-9 ]
  • [ 913358-93-7 ]
YieldReaction ConditionsOperation in experiment
92% (2R)-2-{(15)-6,7-dimethoxy-l-[2-(4-trifluoromethyl-phenyl)-ethyl]-3,4-dihydro-iisoquinolin-2-yl}-N-methyl-2-phenyl-acetamide hydrochloride (I) - almorexant, form A (16 -6,7-Dimethoxy-l-[2-(4-trifluoromethylphenyl)ethyl]-l,2,3,4-tetrahydroisoquinoline hydrochloride (50 g) was suspended in 2-butanone (250 ml) under stirring at the laboratory temperature.' After 5 minutes Na2C03 (30.3 g) was added and the suspension was stirred at the laboratory temperature for another 10 minutes. After adding of (S)-methylcarbamoyl-phenyl- methylester of toluene-4-sulfonic acid (51.7 g) the reaction mixture was heated up to reflux and refluxed while being stirred for 16 hours. Then, most of the solvent (ca. 200 ml) was removed by distillation and the residue was co-distilled with ethyl acetate (3 x 50 ml). Then, the mixture was diluted with 150 ml of ethyl acetate and the solid fraction was aspirated and washed with 100 ml of ethyl acetate. The solution was washed with water (2 x 100 ml) and brine (50 ml). After drying with MgSC*4 the solution was heated up to 60 C. A solution of HCl(g) in ethyl acetate (8.9%, 51 g) was added dropwise within 30 minutes. After heating up to reflux and stirring for 30 minutes the solution was cooled down to 0 C and aspirated. 63 g (92%) of almorexant hydrochloride, form A, were obtained (confirmed by an XRPD analysis).
 

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