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Chemical Structure| 33640-67-4 Chemical Structure| 33640-67-4

Structure of 33640-67-4

Chemical Structure| 33640-67-4

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Product Details of [ 33640-67-4 ]

CAS No. :33640-67-4
Formula : C11H15NO3
M.W : 209.24
SMILES Code : C[C@@H](O)[C@H](N)C(OCC1=CC=CC=C1)=O
MDL No. :MFCD02094351

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Application In Synthesis of [ 33640-67-4 ]

* 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 [ 33640-67-4 ]

[ 33640-67-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 33640-67-4 ]
  • [ 138775-22-1 ]
  • [ 220663-31-0 ]
  • 2
  • [ 6624-49-3 ]
  • [ 33640-67-4 ]
  • benzyl (2S)-2-(1-hydroxylethyl)-2-(isoquinoline-3-carboxamido)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 - 20℃; for 14h;Inert atmosphere; General procedure: At 0 °C and with stirring to the solution of 865 mg (5.0 mmol) of <strong>[6624-49-3]isoquinoline-3-carboxylic acid</strong> in 10 ml of anhydrous THF 675 mg (5.0 mmol) of HOBt was added to form reaction mixture A. The solution of 5.5 mmol of l-amino acid benzylester in 5 ml of anhydrous THF was adjusted pH 9 with triethylamine and stirred for 30 min to form mixture B. At 0 °C the mixtures A and B were mixed and then 1339 mg (6.5 mmol) of DCC was added. The reaction mixture was stirred at 0 °C for 2 h, at room temperature for12 h and TLC (ethyl acetate/petroleum ether, 1:2) indicated the complete disappearance of <strong>[6624-49-3]isoquinoline-3-carboxylic acid</strong>. The formed precipitates of DCU were removed by filtration and the filtrate was evaporated under vacumm. The residue was dissolved in 50 ml of ethyl acetate and the formed solution was washed successively with saturated aqueous solution of NaHCO3 (30 ml .x. 3), 5percent aqueous solution of KHSO4 (30 ml .x. 3) and saturated aqueous solution of NaCl (30 ml .x. 3) and dried over anhydrous Na2SO4. After filtration the filtrate was evaporated under vacumm and the residure was purified on silica gel chromatography (CHCl3:MeOH, 20:1) to give the title compounds.
  • 3
  • [ 73724-48-8 ]
  • [ 33640-67-4 ]
YieldReaction ConditionsOperation in experiment
With piperidine; In N,N-dimethyl-formamide; at 20℃; for 0.333333h; The amino acid N-(9-fluorenylmethoxycarbonyl)-l-threonine benzyl ester 26 (300 mg, 0.69 mmol, prepared from commercially available amino acid Fmoc-l-threonine by treatment with cesium carbonate and benzyl bromide in DMF)59 was treated with 20% piperidine/DMF (1 mL) and stirred for 20 min at room temperature. After concentration in vacuo the residue was purified by column chromatography (EtOAc/hexane 7:3 v/v; MeOH/DCM 1:9 v/v). The obtained product l-threonine benzyl ester 27 (112.6 mg, 0.54 mmol, 78%) was submitted to diazo transfer reaction utilizing the method described by Wong et al.41 Triflyl azide preparation: Sodium azide (0.6 g, 9.23 mmol) was dissolved in distilled water (2.0 mL) with DCM (2.5 mL) and cooled on an ice bath. Triflyl anhydride (0.3 mL, 1.79 mmol) was added slowly over 5 min while stirring continued for 2 h. The mixture was placed in a separatory funnel and the DCM phase was removed. The aqueous portion was extracted with DCM and the organic fractions, containing the triflyl azide, were pooled and washed once with saturated NaHCO3 and used without further purification. Subsequently, l-threonine benzyl ester 27 (112.6 mg, 0.54 mmol) was dissolved in water and treated with CuSO4 (8.6 mg, 0.05 mmol). Methanol (4 mL) and previously prepared triflyl azide in DCM (6 mL) were then added, and the solution was stirred at room temperature overnight. Solvents were then removed under reduced pressure to give a blue-green residue which was suspended in DCM (2 ml) and filtered through a plug of silica gel (3 cm in a Pasteur pipette); silica gel was washed with additional DCM (10 ml) and the combined filtrates were concentrated to give the product 18 as a pale oil in 60% yield (97.3 mg, 0.41 mmol).
 

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