Sodium Bicarbonate → HCID 58135410, compound

HRID 1893585Notes

Reaction equation

HRID 1893585 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:38])=[C:6]([N:8]([CH2:24][C:25]([N:27]([N:29]2[CH2:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:30]2)[CH3:28])=[O:26])[CH2:9][C:10]([NH:12][CH2:13][CH2:14][N:15](C(OC(C)(C)C)=O)[CH3:16])=[O:11])[CH:7]=1.Cl.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:38])=[C:6]([N:8]([CH2:24][C:25]([N:27]([N:29]2[CH2:30][C:31]3[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:37]2)[CH3:28])=[O:26])[CH2:9][C:10]([NH:12][CH2:13][CH2:14][NH:15][CH3:16])=[O:11])[CH:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 68154099HCID 68154099, compound

Product 1

HCID 58135410HCID 58135410, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (294 mg, 0.54 mmol) obtained in step A was dissolved in dichloromethane (5.5 ml), 4N hydrochloric acid-ethyl acetate solution (1.35 ml) was added, and the mixture was stirred at room temperature for 8 hr. The aqueous layer was alkalified by addition of saturated aqueous sodium hydrogen carbonate, and the organic layer was extracted with dichloromethane, and dried over sodium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (NH silica gel use, methanol-dichloromethane) to give the title compound (179 mg, yield 75%) as a pale-yellow amorphous solid.

Workup

  1. extractionthe organic layer was extracted with dichloromethane
  2. dry with materialdried over sodium sulfate
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe solution was concentrated under reduced pressure
  5. customThe obtained oil was purified by silica gel column chromatography (NH silica gel use, methanol-dichloromethane)

Sources & evidence

ORD record
ord-6e7fa4a1e0814136b12d7f10102b513a
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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