Sodium Bicarbonate → HCID 178423631, compound

HRID 470674Notes

Reaction equation

HRID 470674 reaction equation
Cl.O1CCOCC1.[Cl:8][C:9]1[CH:10]=[C:11]([NH:47]C(=O)OC(C)(C)C)[CH:12]=[C:13]([C@@H:15]2[C@@:26]3([C:34]4[C:29](=[CH:30][C:31]([Cl:35])=[CH:32][CH:33]=4)[NH:28][C:27]3=[O:36])[C:18]3([CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH2:19]3)[NH:17][C@H:16]2[C:37](=[O:46])[NH:38][C@H:39]2[CH2:44][CH2:43][C@H:42]([OH:45])[CH2:41][CH2:40]2)[CH:14]=1.C(=O)(O)[O-].[Na+]>O1CCOCC1>[NH2:47][C:11]1[CH:12]=[C:13]([C@@H:15]2[C@@:26]3([C:34]4[C:29](=[CH:30][C:31]([Cl:35])=[CH:32][CH:33]=4)[NH:28][C:27]3=[O:36])[C:18]3([CH2:23][CH2:22][C:21]([CH3:24])([CH3:25])[CH2:20][CH2:19]3)[NH:17][C@H:16]2[C:37]([NH:38][C@H:39]2[CH2:44][CH2:43][C@H:42]([OH:45])[CH2:41][CH2:40]2)=[O:46])[CH:14]=[C:9]([Cl:8])[CH:10]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 178423630HCID 178423630, compound

Product 1

HCID 178423631HCID 178423631, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4N hydrochloric acid/1,4-dioxane solution (1.16 ml, 4.64 mmol) was added to a 1,4-dioxane (6 ml) solution of the compound (321 mg, 0.47 mmol) obtained in Step 3 above and the resulting mixture was stirred at room temperature for 24 hours. Saturated sodium bicarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and then the residue was purified by silica gel column chromatography [methanol:ethyl acetate=1:4 (v/v)] to give 248 mg (91%) of the title compound as a colorless solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography [methanol:ethyl acetate=1:4 (v/v)]

Sources & evidence

ORD record
ord-57cdf48db6c3409195c55b08c7b60cc6
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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