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Chemical Structure| 2378259-33-5 Chemical Structure| 2378259-33-5

Structure of 2378259-33-5

Chemical Structure| 2378259-33-5

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Product Details of [ 2378259-33-5 ]

CAS No. :2378259-33-5
Formula : C12H14ClNO3
M.W : 255.70
SMILES Code : O=C(O)CNC1=CC(C2(C)CC2)=C(Cl)C=C1O
English Name :(4-Chloro-2-hydroxy-5-(1-methylcyclopropyl)phenyl)glycine

Safety of [ 2378259-33-5 ]

Application In Synthesis of [ 2378259-33-5 ]

* 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 [ 2378259-33-5 ]

[ 2378259-33-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 178311-48-3 ]
  • [ 2378259-33-5 ]
  • [ 2378259-34-6 ]
YieldReaction ConditionsOperation in experiment
85% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In 2-methyltetrahydrofuran; ethyl acetate at -20 - -10℃; for 1h; 1.g-1; 9 Step g-1: Compound H-1 (60.6 g, 0.237 mol) and compound I-1 (1-tert-butoxycarbonyl-3- (1-piperazinyl) azetidine, 57.2 g, 0.237 mol)And N, N-diisopropylethylamine (126mL, 0.711mol) were dissolved in anhydrous methyltetrahydrofuran (1.5L),Reduce the temperature to -20 -10 , then slowly add 50% T3P / ethyl acetate solution (180mL, 284.4mmol), and react at -20 -10 for 1h.TLC monitors the disappearance of raw materials. Control the reaction temperature <-10 , slowly add water (1.5L), warm to room temperature after the addition, separate the organic phase,The aqueous phase was extracted with DCM / MeOH (10: 1, 1.5 L × 2). The combined organic phases were dried, filtered, and concentrated to give a crude yellow solid.Purification by column chromatography (DCM / MeOH = 40: 1) to obtain yellow pure solid compound J-1 (96.5 g, yield: 85%,
43% With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine at 20℃; for 1h; 8 Step 8: Preparation of tert-butyl 3-(4-((4-chloro-2-hydroxy-5-(l- methylcyclopropyl)phenyl)glycyl)piperazin- 1 -yl)azetidine- 1 -carboxylate To a solution of tert-butyl 3-(piperazin-l-yl)azetidine-l-carboxylate (250 mg, 1.03 mmol) were added DIEA (530 mg, 4.1 mmol), (4-chloro-2-hydroxy-5-(l- methylcyclopropyl)phenyl)glycine (290 mg, 1.13 mmol) and PyBOP (1.07 g, 2.06 mmol). The mixture was stirred at 20°C for 1 hour. The mixture was quenched with water and extracted with EtOAc. The organic layer was washed with brine, dried over Na2S04 and concentrated. The residue was purified by column chromatography on silica gel with DCM: MeOH (50:1-20:1) to give tert-butyl 3-(4-((4-chloro-2-hydroxy-5-(l-methylcyclopropyl)phenyl)glycyl)piperazin-l- yl)azetidine-l-carboxylate (210 mg, yield: 43%) as a brown oil. LC/MS (ESI) m/z 479.2 [M+l] +; 1H-NMR (400MHz, CDCb) d 6.84-6.79 (m, 1H), 6.43 (s, 1H), 3.96-3.88 (m, 4H), 3.82-3.79 (m, 2H), 3.71 (s, 2H), 3.48 (d, J = 4.0 Hz, 2H), 3.11-3.08 (m, 1H), 2.36 (d, J = 4.0 Hz, 4H), 1.93 (s, 2H), 1.82-1.73 (m, 3H), 1.41 (s, 9H), 1.26-1.23 (m. 2H).
  • 2
  • [ 2378259-33-5 ]
  • [ 1629268-00-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / 2-methyltetrahydrofuran; ethyl acetate / 1 h / -20 - -10 °C 2: hydrogenchloride / ethanol; water / 16 h / 45 °C 3: triethylamine / tetrahydrofuran; water; aq. phosphate buffer / 2 h / 20 °C / pH 7.14 - 7.37
 

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