Sodium Bicarbonate → HCID 15434246, compound

HRID 849229Notes

Reaction equation

HRID 849229 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([S:8][CH2:9][C:10]2[N:15]=[C:14]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24]C)[CH:19]=3)[CH:13]=[C:12]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[CH:11]=2)=[N:5][N:4]=1)[CH3:2].C(=O)([O-])O.[Na+]>C(Cl)Cl.B(Br)(Br)Br>[CH2:1]([C:3]1[S:7][C:6]([S:8][CH2:9][C:10]2[N:15]=[C:14]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=3)[CH:13]=[C:12]([N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[CH:11]=2)=[N:5][N:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 15434245HCID 15434245, compound

Product 1

HCID 15434246HCID 15434246, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 25134Boron tribromideSolvent

Conditions

Temperature
2 °C

Procedure

To a solution of the compound (18.2 mg) obtained in Example 2 in methylene chloride (0.5 ml), boron tribromide (a 1.0M methylene chloride solution, 0.30 ml) was added at -78° C., and the temperature was raised to about 2° C. over a period of 3.6 hours. Then, a saturated sodium hydrogen carbonate aqueous solution (20 ml) was added thereto. The reaction solution was extracted with ethyl acetate, and the organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by thin layer chromatography for separation (silica gel 60F254, manufactured by Merck Company, chloroform:methanol=10:1) to obtain the above identified compound (14.9 mg) as a colorless oily substance.

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate
  2. washthe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was purified by thin layer chromatography for separation (silica gel 60F254, manufactured by Merck Company, chloroform:methanol=10:1)
  6. customto obtain the

Sources & evidence

ORD record
ord-0b4bce2c9ce642dc9f7951d3305338fe
Source dataset
uspto-grants-2000_01
Patent number
US06011039

Reaction notes

Loading…