Water → HCID 22180236, compound

HRID 1836819Notes

Reaction equation

HRID 1836819 reaction equation
[CH2:1]([N:8]([CH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1)[C:9](=[O:39])[C:10]1[CH:15]=[C:14]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH:24]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:18][CH2:17]2)[CH:13]=[CH:12][C:11]=1[O:37]C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.O.C(=O)([O-])O.[Na+]>ClCCl>[CH2:1]([N:8]([CH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1)[C:9](=[O:39])[C:10]1[CH:15]=[C:14]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:18][CH2:17]2)[CH:13]=[CH:12][C:11]=1[OH:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 22180530HCID 22180530, compound

Product 1

HCID 22180236HCID 22180236, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

The compound (46 mg) prepared in Example 70 was dissolved in dichloromethane (3.8 ml). A 1 M solution (0.23 ml) of boron tribromide in dichloromethane was added to the solution at 0° C. The mixture was stirred at 0° C. for 20 min, and was then stirred at room temperature for 30 min. Water and a saturated aqueous sodium hydrogencarbonate solution were added to the reaction solution, and the mixture was extracted with dichloromethane, followed by washing with saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under the reduced pressure. The residue was developed by preparative TLC (chloroform:methanol=20:1) to give the title compound (35 mg).

Workup

  1. stirringwas then stirred at room temperature for 30 min
  2. extractionthe mixture was extracted with dichloromethane
  3. washby washing with saturated brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customThe solvent was then removed by distillation under the reduced pressure

Sources & evidence

ORD record
ord-3e197cad6eba450b9a5a2856035a4fc1
Source dataset
uspto-grants-2004_08
Patent number
US06777414B1

Reaction notes

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