Ammonium Chloride → HCID 50899581, compound

HRID 1847109Notes

Reaction equation

HRID 1847109 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[O:14][C:15](=[O:29])[CH:16]4[C@:21]([C:23]=3[CH2:24][CH2:25]2)([CH3:22])[CH2:20][CH2:19][C:18](=[O:28])[CH2:17]4)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[BH4-].[Na+].[Cl-].[NH4+]>CO.ClCCl>[OH:28][C@H:18]1[CH2:19][CH2:20][C@@:21]2([CH3:22])[C@@H:16]([C:15](=[O:29])[O:14][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]([CH3:3])[CH3:1])[CH2:10][CH2:11]4)[CH2:17]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 67609998HCID 67609998, compound

Product 1

HCID 50899581HCID 50899581, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 1 (400 mg, 0.999 mmol) obtained in Example 1 was dissolved in a mixed solvent of methanol (6.0 mL) and dichloromethane (4.0 mL), and sodium borohydride (37.8 mg, 0.999 mmol) was added thereto at 0° C., followed by stirring at 20 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 silica gel column chromatography to obtain the title compound (363 mg, 90%).

Workup

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

Sources & evidence

ORD record
ord-174597a7beeb42cb85d9dd830d81ad80
Source dataset
uspto-grants-2015_02
Patent number
US08952003B2

Reaction notes

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