Ammonium Hydroxide → HCID 18655859, compound

HRID 1708454Notes

Reaction equation

HRID 1708454 reaction equation
[CH2:1]([N:4]([CH:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][C:23]=2[O:27]C)[CH2:18]1)[CH2:5][CH2:6][CH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[O:8]1)[CH2:2][CH3:3].Cl.N1C=CC=CC=1.[NH4+].[OH-]>O>[CH2:1]([N:4]([C@@H:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][C:23]=2[OH:27])[CH2:18]1)[CH2:5][CH2:6][C@H:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[O:8]1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 10176127Pyridinium chlorideHCID 15284313HCID 15284313, compound

Product 1

HCID 18655859HCID 18655859, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The product of Example 35 and excess pyridine hydrochloride were heated in an oil bath at 200° C. for 1 hr. The reaction was cooled, diluted with H2O, basified with NH4OH and extracted with ether. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was subjected to flash chromatography (Silica: 6:4 pet ether/EtOAc) and the product [upper isomer by TLC (Silica: 1:1 pet ether/EtOAc) showed characteristic peaks at: NMR (300 MHz, CDCl3) δ7.9-6.6(m, 7H), 5.7(dd, 1H), 0.9(t, 3H).

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with ether
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b3ad2e0088dd42189d813ccebb9f9035
Source dataset
uspto-grants-1994_10
Patent number
US05358971

Reaction notes

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