Sodium Bicarbonate → HCID 66857634, compound

HRID 1888308Notes

Reaction equation

HRID 1888308 reaction equation
[CH3:1][C@@H:2]1[O:6][C:5](=[O:7])[N:4]([CH2:8][CH2:9][S:10][C:11]2[S:12][CH:13]=[C:14]([C:16]([O:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:17])[N:15]=2)[C@H:3]1/[CH:23]=[CH:24]/[CH2:25][C:26]([CH3:37])([O:32][Si](C)(C)C)[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].Cl.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[OH:32][C:26]([CH3:37])([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:25]/[CH:24]=[CH:23]/[C@H:3]1[C@H:2]([CH3:1])[O:6][C:5](=[O:7])[N:4]1[CH2:8][CH2:9][S:10][C:11]1[S:12][CH:13]=[C:14]([C:16]([O:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:17])[N:15]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 68768429HCID 68768429, compound

Product 1

HCID 66857634HCID 66857634, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound 43 (6.53 g) in ethyl acetate (114 mL) was slowly added dropwise 4N hydrogen chloride/ethyl acetate solution (14 mL) at 0° C. and the solution was stirred for 10 minutes. An aqueous saturated sodium bicarbonate solution was slowly added dropwise to the reaction solution, which was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was purified by Yamazen Parallel Prep (Brand name; column: 3 L, inject column: 2 L, n-hexane:ethyl acetate=40:60) to give the title compound (3.81 g) having the following physical data.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated sodium bicarbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe obtained residue was purified by Yamazen Parallel Prep (Brand name; column: 3 L, inject column: 2 L, n-hexane:ethyl acetate=40:60)

Sources & evidence

ORD record
ord-323aa24162de4715947ea17318744b32
Source dataset
uspto-grants-2013_08
Patent number
US08501793B2

Reaction notes

Loading…