Ethyl Acetate → HCID 86753794, compound

HRID 1417603Notes

Reaction equation

HRID 1417603 reaction equation
[OH:1][CH:2]1[C:10]2[C:9]3[O:11][C@@:12]45[CH2:22][CH2:21][C@H:20]([OH:23])[C:19]([CH3:25])([CH3:24])[C@@H:18]4[CH2:17][CH2:16][C@H:15]([CH3:26])[C@@:13]5([CH3:27])[CH2:14][C:8]=3[C:7]([OH:28])=[CH:6][C:5]=2[C:4](=[O:29])[NH:3]1.[C:30]1(C)[CH:35]=CC(S([O-])(=O)=O)=C[CH:31]=1.[NH+]1C=CC=CC=1.C(OCC)(=O)C>C(O)CC>[OH:28][C:7]1[C:8]2[CH2:14][C@:13]3([CH3:27])[C@@H:15]([CH3:26])[CH2:16][CH2:17][C@H:18]4[C:19]([CH3:25])([CH3:24])[C@@H:20]([OH:23])[CH2:21][CH2:22][C@@:12]34[O:11][C:9]=2[C:10]2[CH:2]([O:1][CH2:31][CH2:30][CH3:35])[NH:3][C:4](=[O:29])[C:5]=2[CH:6]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86753795HCID 86753795, compound

Product 1

HCID 86753794HCID 86753794, compoundYield 207.7%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

To a solution of Compound (30a) (33 mg, 0.08 mmol) in 3.0 ml of 1-propanol was added 6 mg of pyridinium p-toluenesulfonate, and the mixture stirred at room temperature for one hour. To the reaction was added 20 ml of ethyl acetate. The mixture was washed with saturated brine, and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by a column chromatography (Merck, Lobar column, size A; ethyl acetate), and by crystallization from ethyl acetate to give 22 mg (60%) of Compound (30c).

Workup

  1. washThe mixture was washed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationAfter concentration under reduced pressure
  4. customthe residue was purified by a column chromatography (Merck, Lobar column, size A
  5. customethyl acetate), and by crystallization from ethyl acetate

Sources & evidence

ORD record
ord-58071c6ce1a14f4084ba8afbc207b010
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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