Diethyl Ether → HCID 59134335, compound

HRID 1993482Notes

Reaction equation

HRID 1993482 reaction equation
C(=O)(O[C@H:4]1[C:17]2[CH:16]=[C:15]3[C:10]([N:11]([CH3:27])[C:12](=[O:26])[CH:13](CCC4C=CC=CC=4)[O:14]3)=[C:9](C(C)(C)C)[C:8]=2[O:7][C:6]([CH3:33])([CH3:32])[C@@H:5]1[OH:34])N.C(=O)([O-])O.[Na+].CCO[CH2:44][CH3:45]>Cl.O1CCOCC1>[OH:34][C@@H:5]1[C@@H:4]([NH:11][CH2:10][CH2:9][C:45]2[CH:44]=[CH:6][CH:5]=[CH:4][CH:17]=2)[C:17]2[CH:16]=[C:15]3[C:10]([N:11]([CH3:27])[C:12](=[O:26])[CH2:13][O:14]3)=[CH:9][C:8]=2[O:7][C:6]1([CH3:32])[CH3:33]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 86617189HCID 86617189, compound

Product 1

HCID 59134335HCID 59134335, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

To a solution of t-butyl(2-phenylethyl)(7R*,8S*)-[7-hydroxy-4,6,6-trimethyl-3-oxo-4,6,7,8-tetrahydro-1,5-dioxa-4-aza-anthracene-8-yl] carbamate (115 mg, 0.24 mmol) in ether (2.2 mL), 4 mol/L hydrogen chloride-dioxane (500 μL) was added at room temperature, and the resulting mixture was stirred at room temperature for 5 hours and then at 50° C. for 30 minutes. Upon the completion of the reaction, saturated aqueous sodium hydrogencarbonate solution was added thereto, the resulting solution was extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The resulting mixture was purified by silica gel column (hexane/ethyl acetate=1/2) and the aimed product was obtained (yield: 76%).

Workup

  1. waitat 50° C. for 30 minutes
  2. additionwas added
  3. extractionthe resulting solution was extracted with ethyl acetate
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting mixture was purified by silica gel column (hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-ebce5874c9534245a9660743d0ac9ecf
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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