Sodium Bicarbonate → HCID 69722150, compound

HRID 2307717Notes

Reaction equation

HRID 2307717 reaction equation
C([O:4][C:5]1[CH:13]=[C:12]([C:14]([N:16]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:35]3[CH:40]=[CH:39][C:38](Cl)=[CH:37][CH:36]=3)[CH:29]=2)[C@@H:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][CH2:19][CH2:18]2)=[O:15])[C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[C:42]([OH:44])=[O:43])(=O)C.C([O-])(O)=O.[Na+]>CO.O>[OH:4][C:5]1[CH:13]=[C:12]([C:14]([N:16]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:29]=2)[C@@H:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][CH2:19][CH2:18]2)=[O:15])[C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[C:42]([OH:44])=[O:43]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 69721153HCID 69721153, compound

Product 1

HCID 69722150HCID 69722150, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The products from Example 104B (0.97 g, 1.68 mmol) in methanol (60 mL) were treated with NaHCO3 (3.9 g, 46.4 mmol) in water (30 mL) and the mixture was stirred at room temperature for 24 hours. The methanol was removed under reduced pressure and the remaining aqueous solution was acidified to pH 1 with 1N HCl. The acidified solution was extracted with ethyl acetate (5×15 mL). The organic extracts were combined, washed with brine (10 mL), dried over Na2SO4, filtered and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 9:1 CH2Cl2:methanol to 8:2 CH2Cl2:methanol) to provide the title compounds as a foamy white solid (208 mg, 23%).

Workup

  1. customThe methanol was removed under reduced pressure
  2. extractionThe acidified solution was extracted with ethyl acetate (5×15 mL)
  3. washwashed with brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (silica gel, 9:1 CH2Cl2:methanol to 8:2 CH2Cl2:methanol)

Sources & evidence

ORD record
ord-e7ab818ab45549dfa9d6169a992ec068
Source dataset
uspto-grants-2004_12
Patent number
US06831193B2

Reaction notes

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