Sodium Bicarbonate → HCID 66590252, compound

HRID 1092806Notes

Reaction equation

HRID 1092806 reaction equation
[CH:1]1([N:4]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:35]=2[Cl:41])[C:5]([C:7]2[C@@H:8]([CH2:31][OH:32])[NH:9][CH2:10][CH2:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][O:22][C:23]3[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:30])=[CH:15][CH:14]=2)=[O:6])[CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].[C:47](=O)([O:53]C(C)(C)C)[O:48][C:49]([CH3:52])([CH3:51])[CH3:50]>O1CCOCC1>[CH:1]1([N:4]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:35]=2[Cl:41])[C:5]([C:7]2[C@@H:8]([CH2:31][OH:32])[NH:9][CH2:10][CH2:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][O:22][C:23]3[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:30])=[CH:15][CH:14]=2)=[O:6])[CH2:3][CH2:2]1.[CH:1]1([N:4]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:35]=2[Cl:41])[C:5]([C:7]2[C@@H:8]([CH2:31][OH:32])[N:9]([C:47]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:53])[CH2:10][CH2:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][O:22][C:23]3[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:30])=[CH:15][CH:14]=2)=[O:6])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 56849261HCID 56849261, compound

Product 2

HCID 56849261HCID 56849261, compoundHCID 66590252HCID 66590252, compoundYield 147.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound 6 was prepared as described in Example 10. Into a 10 mL round bottom flask was added Compound 6 (546 mg, 858 μmol) and dioxane (1.9 mL). The reaction was added sodium bicarbonate (180 mg, 2.15 mmol) and di-tert-butyl carbonate (337 mg, 1.54 mmol). The reaction was stirred overnight at room temperature. Solvent was removed under vacuum and the residue partitioned between water (10 mL) and ethyl acetate (10 mL). The organic layer was separated and the aqueous layer was extracted further with ethyl acetate (2×10 mL). The organic layers were combined and dried over sodium sulfate. The solution was filtered and solvent removed under vacuum. The residue was purified by column chromatography (0->2% MeOH/DCM) to give 19A (465 mg, 74%). ESI-MS:m/z 735.3 (M+H)+

Workup

  1. customSolvent was removed under vacuum
  2. customthe residue partitioned between water (10 mL) and ethyl acetate (10 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted further with ethyl acetate (2×10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationThe solution was filtered
  7. customsolvent removed under vacuum
  8. customThe residue was purified by column chromatography (0->2% MeOH/DCM)

Sources & evidence

ORD record
ord-f19c798659c646eaa2bea0ddf36b33b4
Source dataset
uspto-grants-2012_03
Patent number
US08129538B1

Reaction notes

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