Ammonium Chloride → HCID 67609803, compound

HRID 1847112Notes

Reaction equation

HRID 1847112 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[CH:16]([CH2:17][C:18](=[O:28])[CH2:19][CH2:20]2)[C:15](=[O:29])C=3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[OH2:30].O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+].[Cl-].[NH4+]>CO>[OH:28][C@@H:18]1[CH:19]=[CH:20][C@@:21]2([CH3:22])[C@@H:16]([C:15](=[O:30])[O:29][C:13]3[C@H:12]4[C@:26]([CH3:27])([CH2:25][CH2:24][C:23]=32)[C@@H:9]([C@H:7]([CH3:8])[CH2:6][CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:10][CH2:11]4)[CH2:17]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 21585214Cerium trichloride heptahydrateHCID 67609435HCID 67609435, compound

Product 1

HCID 67609803HCID 67609803, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 4 (19 mg, 0.048 mmol) obtained in Example 4 was suspended in methanol (1.0 mL), and cerium chloride heptahydrate (36 mg, 0.096 mmol) and sodium borohydride (0.9 mg, 0.024 mmol) were added thereof at 0° C., followed by stirring at room temperature for 10 minutes. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate twice. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to yield a residue. The residue was purified by preparative thin layer chromatography to obtain the title compound (17 mg, 91%).

Workup

  1. customat 0° C.
  2. extractionfollowed by extraction with ethyl acetate twice
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto yield a residue
  7. customThe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-cbd79ce69b8a4fd089974c7fd5a281bb
Source dataset
uspto-grants-2015_02
Patent number
US08952003B2

Reaction notes

Loading…