Ammonium Chloride → HCID 89555413, compound

HRID 928663Notes

Reaction equation

HRID 928663 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[CH:23]=[C:24]([CH:39]=[CH:40][CH:41]=3)[C:25]([N:27]3[CH2:38][CH2:37][CH2:36][C@H:28]3[C:29]([O:31]C(C)(C)C)=[O:30])=[O:26])=[CH:16][CH:15]=2)[CH:5]=[C:6]([O:9][CH2:10][C:11](=[O:13])[CH3:12])[C:7]=1[F:8].[BH4-].[Na+].[Cl-].[NH4+]>CO>[F:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:21][C:22]3[CH:23]=[C:24]([CH:39]=[CH:40][CH:41]=3)[C:25]([N:27]3[CH2:38][CH2:37][CH2:36][C@H:28]3[C:29]([OH:31])=[O:30])=[O:26])=[CH:18][CH:19]=2)[CH:5]=[C:6]([O:9][CH2:10][CH:11]([OH:13])[CH3:12])[C:7]=1[F:8]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 117689882HCID 117689882, compound

Product 1

HCID 89555413HCID 89555413, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (1.5 mL) of the compound (66.0 mg, 0.117 mmol) of Step 1 of Example 49 in methanol, sodium borohydride (5.3 mg, 0.14 mmol) was added, and stirred at room temperature for 1 hour. After a saturated aqueous ammonium chloride solution was added to the reaction solution, the mixture was concentrated under reduced pressure, and extracted with ethyl acetate. The organic phase was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. After that, the solvent was distilled away under reduced pressure. The resulting residue was dissolved in dichloromethane (2 mL), and trifluoroacetic acid (1 mL) was added thereto, and stirred at room temperature for 1 hour. The solvent was distilled away under reduced pressure. The resulting residue was purified by reversed-phase HPLC in the same manner as in Step 2 of Example 1, to thus obtain the title compound.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter that, the solvent was distilled away under reduced pressure
  6. dissolutionThe resulting residue was dissolved in dichloromethane (2 mL)
  7. additiontrifluoroacetic acid (1 mL) was added
  8. stirringstirred at room temperature for 1 hour
  9. distillationThe solvent was distilled away under reduced pressure
  10. customThe resulting residue was purified by reversed-phase HPLC in the same manner as in Step 2 of Example 1

Sources & evidence

ORD record
ord-77af084ecfd04e35a06732b455912d53
Source dataset
uspto-grants-2016_03
Patent number
US09290487B2

Reaction notes

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