Sodium Bicarbonate → HCID 131718237, compound

HRID 256781Notes

Reaction equation

HRID 256781 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:25](=[O:26])[N:6]2[C:7]([C:13]([O:15]CC3C=CC(OC)=CC=3)=[O:14])=[C:8]([CH:11]=[CH2:12])[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].C(=O)(O)[O-].[Na+:31]>C1(OC)C=CC=CC=1.ClCCl.P([O-])([O-])([O-])=O>[OH:1][C@@H:2]([C@H:4]1[C:25](=[O:26])[N:6]2[C:7]([C:13]([O-:15])=[O:14])=[C:8]([CH:11]=[CH2:12])[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[Na+:31]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 131718239HCID 131718239, compound

Product 1

HCID 131718237HCID 131718237, compoundYield 23.5%

Reagents, catalysts & solvents 3

HCID 1061PhosphateSolventHCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

to -60° C. To this mixture was added a solution of 33.7 mg (0.0944 mmol) of the compound prepared in Example 5 in 1.4 ml of anisole and 0.2 ml of dichloromethane, and the mixture was stirred for 30 minutes at the same temperature. And then, to the mixture was added a solution of 143 mg (1.7 mmol) of sodium bicarbonate in 4 ml of 0.1 M phosphate buffer (pH 7.0), and the mixture was stirred for 30 minutes under ice-cooling. After the reaction mixture was filtered, the filtration was washed twice with dichloromethane. The aqueous layer was separated, and purified by reverse phase silica gel column chromatography (elution with 10% methanol-water) to give 5.74 mg (yield: 23.5% of the title compound.

Workup

  1. customto -60° C
  2. stirringthe mixture was stirred for 30 minutes under ice-
  3. temperaturecooling
  4. filtrationAfter the reaction mixture was filtered
  5. filtrationthe filtration
  6. washwas washed twice with dichloromethane
  7. customThe aqueous layer was separated
  8. custompurified by reverse phase silica gel column chromatography (elution with 10% methanol-water)

Sources & evidence

ORD record
ord-f020786680b5420e90295980d350b825
Source dataset
uspto-grants-1993_11
Patent number
US05258509

Reaction notes

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