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Chemical Structure| 1221343-14-1 Chemical Structure| 1221343-14-1

Structure of 1221343-14-1

Chemical Structure| 1221343-14-1

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Product Details of [ 1221343-14-1 ]

CAS No. :1221343-14-1
Formula : C8H7BO4
M.W : 177.95
SMILES Code : O=C(C1=CC=C2C(B(O)OC2)=C1)O
MDL No. :MFCD20527893
InChI Key :VXDGEAYKTHEYPI-UHFFFAOYSA-N
Pubchem ID :58404071

Safety of [ 1221343-14-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 1221343-14-1 ]

* 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 [ 1221343-14-1 ]

[ 1221343-14-1 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 42872-74-2 ]
  • [ 1221343-14-1 ]
  • 2
  • [ 89891-69-0 ]
  • [ 1221343-14-1 ]
  • 4
  • [ 170230-88-3 ]
  • [ 1221343-14-1 ]
  • 5
  • [ 876189-18-3 ]
  • [ 1221343-14-1 ]
  • 6
  • [ 1221343-14-1 ]
  • [ 1397-89-3 ]
  • C55H78BNO20 [ No CAS ]
YieldReaction ConditionsOperation in experiment
20.5% With triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; at 20℃; for 12h;pH 8; General procedure: 3?-N-acyl derivatives ofAmB (5-7) were prepared by the treatment of the unprotected AmB (1) withN-hydroxysuccinimide ester (-OSu) of the 3-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-7-yl)propionic acid, 1-hydroxy-1,3- dihydrobenzo[c][1,2]oxaborol-6-yl)carboxylic acid or 1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)carboxylic acid which were obtained by the standard method using DCC.To a stirred solution of AmB (1) (150 mg, 0.162 mmol) in DMSO(100 mg ml- 1) were added the solution of N-hydroxysuccinimide ester ofthe corresponding acid (5 eq) in the mixture of DMF-CH2Cl2 (2:1)(150 mg ml- 1) and Et3N to pH 8. The reaction mixture was stirred for 12 hat room temperature, and then fivefold volume of Et2O was added. Theresulting mixture was shaken intensively to partially extract DMSO and DMF,and the layer of Et2O was separated. This procedure was repeated twice. To the obtained dark yellow oil, n-BuOH (20 ml) saturated with H2O was added andthe resultant solution was washed with H2O (10 ml). This procedure wasrepeated twice. The organic layer was evaporated in vacuum with 0.6 eq of H2Oto the volume~ 1 ml n-BuOH solution. The organic layer was poured into astirring mixture of Et2O to precipitate the crude reaction product. Theprecipitate was filtered, washed with Et2O and dried in vacuum to give ayellow powder. Crude products (5-7) were purified by the column chromatographymethod on silica gel in CHCl3MeOHH2OHCOOH(5:1:0.01:0.01, v/v) system. The yields of the pure N-acyl-derivatives (3-5)were: 40 mg (22%) for 3, 36 mg (20.5%) for 4 and 32 mg (18%) for 5.
  • 7
  • [ 1221343-14-1 ]
  • [ 39796-52-6 ]
  • N-(2-(benzylamino)-2-oxoethyl)-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% To a solution of1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-6-carboxylic acid (136.3 mg, 0.766mmol) in N,N-dimethylformamide (7.2 mL) was added N-methylmorpholine (421 µL,3.83 mmol) and HATU (320 mg, 0.843 mmol).The solution was stirred for 5 minutes, and then<strong>[39796-52-6]2-amino-N-benzylacetamide</strong> (126 mg, 0.766 mmol) was added. The solution was stirred for 4 h, and thenHOAc (1 mL) was added. The solution waspurified directly by automated gradient reverse phase liquid chromatography(10% to 100% MeCN-water). The desiredfractions were combined and concentrated in vacuo. The residue was triturated with MeCN (5 mL),and the solid was collected by vacuum filtration and dried under high vacuum toafford 43.7 mg of N-(2-(benzylamino)-2-oxoethyl)-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-6-carboxamide (18% yield) as a yellow solid.LCMS: [M+H]+: 324.9.
 

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