Sodium Bicarbonate → HCID 57226268, compound

HRID 487825Notes

Reaction equation

HRID 487825 reaction equation
[CH2:1]([CH:4]1[CH:30]=[C:29]([CH3:31])[CH2:28][CH:27]([CH3:32])[CH2:26][CH:25]([O:33][CH3:34])[CH:24]2[O:35][C:20]([OH:39])([CH:21]([CH3:38])[CH2:22][CH:23]2[O:36][CH3:37])[CH:19]([OH:40])[C:18](=[O:41])[N:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:11](=[O:42])[O:10][CH:9]([C:43]([CH3:53])=[CH:44][CH:45]2[CH2:50][CH2:49][CH2:48][CH:47]([O:51][CH3:52])[CH2:46]2)[CH:8]([CH3:54])[CH:7]([O:55][Si:56]([C:59]([CH3:62])([CH3:61])[CH3:60])([CH3:58])[CH3:57])[CH2:6][C:5]1=[O:63])[CH:2]=[CH2:3].C(=O)([O-])O.[Na+]>C(O)(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:1]([CH:4]1[CH:30]=[C:29]([CH3:31])[CH2:28][CH:27]([CH3:32])[CH2:26][CH:25]([O:33][CH3:34])[CH:24]2[O:35][C:20]([OH:39])([CH:21]([CH3:38])[CH2:22][CH:23]2[O:36][CH3:37])[C:19](=[O:40])[C:18](=[O:41])[N:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:11](=[O:42])[O:10][CH:9]([C:43]([CH3:53])=[CH:44][CH:45]2[CH2:50][CH2:49][CH2:48][CH:47]([O:51][CH3:52])[CH2:46]2)[CH:8]([CH3:54])[CH:7]([O:55][Si:56]([C:59]([CH3:60])([CH3:61])[CH3:62])([CH3:57])[CH3:58])[CH2:6][C:5]1=[O:63])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 57047944HCID 57047944, compound

Product 1

HCID 57226268HCID 57226268, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A solution of the product of step (b) (85 mg) in glacial acetic acid (10 ml) containing copper (II) acetate (1 g) was heated at 80° C. for 5 minutes. The cooled reaction mixture was then poured into saturated aqueous sodium hydrogen carbonate solution and this was extracted with diethyl ether. The ether extracts were then dried (MgSO4), filtered and concentrated to an oil in vacuo. Chromatography on silica eluting with acetone/hexane [2:5] then gave the subtitle compound as a foam (40 mg).

Workup

  1. customThe cooled reaction mixture
  2. extractionthis was extracted with diethyl ether
  3. dry with materialThe ether extracts were then dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to an oil in vacuo

Sources & evidence

ORD record
ord-b0105aec773947408bf2f3d4566ee303
Source dataset
uspto-grants-1994_03
Patent number
US05296489

Reaction notes

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