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Chemical Structure| 1155425-68-5 Chemical Structure| 1155425-68-5

Structure of 1155425-68-5

Chemical Structure| 1155425-68-5

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Product Details of [ 1155425-68-5 ]

CAS No. :1155425-68-5
Formula : C23H33BO5
M.W : 400.32
SMILES Code : O=C(OC(C)(C)C)C1=CC=CC(CB2O[C@@]3([H])[C@@]([C@](C4)([H])C(C)(C)[C@]4([H])C3)(C)O2)=C1OC
MDL No. :MFCD31382282

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Application In Synthesis of [ 1155425-68-5 ]

* 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 [ 1155425-68-5 ]

[ 1155425-68-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 67-56-1 ]
  • [ 1155425-68-5 ]
  • [ 549506-47-0 ]
  • 4-[2-(3-tert-butoxycarbonyl-2-methoxyphenyl)-1-(2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]dec-4-yl)ethylcarbamoyl]methyl}-3-oxopiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% A solution of dichloromethane (0.58 mL, 9.08 mmol) in THF (6.2 mL) under argon was cooled to -100C (MeOH, liquid N2 slush bath). n-BuLi (3.9 mL, 2.5M in hexane, 7.80 mmol) was added dropwise over 15 minutes and the reaction stirred at -100C for 30 minutes. A THF (5.7 mL) solution of 2-Methoxy-3-(2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]dec-4-ylmethyl)benzoic acid tert-butyl ester (2.13 g, 5.33 mmol) was added dropwise over 15 minutes. After 10 minutes, the cooling bath was removed and the reaction stirred at 0C for 1 h. The reaction was then cooled to -78C for 30 minutes. LiHMDS (8.0 mL, 1.0M in THF, 8.0 mmol) was added dropwise over 10 minutes and the reaction allowed to slowly warm to room temperature while stirring overnight. Upon cooling to -10C, anhydrous MeOH (0.28 mL, 6.92 mmol) was added and the reaction stirred at -10C for 1 h then warmed to room temperature for 1 h. [00193] To a separate dry round bottom flask under argon containing 4-N-Boc-2-oxopiperazine-1-acetic acid (0.318 g, 1.23 mmol) and DCM (3.4 mL) was added N- methylmorpholine (0.20 mL, 1.82 mmol) and HATU (0.494 g, 1.70 mmol). DMF (1.6 mL) was added to make the reaction homogeneous. The reaction was stirred at room temperature for 3 h. A portion of the solution (-2.44 mmol) prepared above was added slowly at 0C and the reaction was gradually warmed to room temperature and stirred for 44 h. The reaction was quenched with H2O and extracted with EtOAc (3x). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by a reverse phase preparative HPLC [Waters Sunfire CI 8 OBD, 5 μιη, 19x50mm, 5-100% AcCN:H20 (with 0.1% TFA)] to afford 0.158 g (19%) of product. ESI-MS m/z 670 (MH)+.
 

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