Sodium Bicarbonate → HCID 86761914, compound

HRID 446581Notes

Reaction equation

HRID 446581 reaction equation
[C:1]1([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:51])[O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]([C:20](=[O:50])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]2[CH:32]=[CH:31][C:30]([C:33](=[O:49])[N:34]([CH2:37][CH2:38][CH2:39][N:40](C(OC(C)(C)C)=O)[CH3:41])[O:35][CH3:36])=[CH:29][CH:28]=2)[CH3:19])[CH2:12][CH2:11]1.Cl.O1CCOCC1.C(=O)([O-])O.[Na+]>O1CCOCC1.CO>[C:1]1([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:51])[O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]([C:20](=[O:50])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]2[CH:28]=[CH:29][C:30]([C:33](=[O:49])[N:34]([O:35][CH3:36])[CH2:37][CH2:38][CH2:39][NH:40][CH3:41])=[CH:31][CH:32]=2)[CH3:19])[CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 86761915HCID 86761915, compound

Product 1

HCID 86761914HCID 86761914, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

The compound (130 mg, 0.165 mmol) obtained in Example 87b was dissolved in a mixed solvent of 1,4-dioxane (1.6 mL) and methanol (1.6 mL), a 4 N hydrochloric acid-dioxane solution (0.412 mL, 1.65 mmol) was added, and the mixture was stirred at room temperature for 4 hours. After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution was added, the mixture was extracted (×3) with methylene chloride, and the resulting organic layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by NH silica gel column chromatography to give the title compound (48 mg; yield, 42%) as a colorless oily substance.

Workup

  1. extractionthe mixture was extracted (×3) with methylene chloride
  2. dry with materialthe resulting organic layer was dried with anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe resulting residue was purified by NH silica gel column chromatography

Sources & evidence

ORD record
ord-4d9adaa65527409f929ffec46b82989c
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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