Ammonium Chloride → HCID 9910903, compound

HRID 649767Notes

Reaction equation

HRID 649767 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[CH2:23][CH2:22][C:21](=[O:24])[C:20]4[N:25]([CH3:28])[CH:26]=[CH:27][C:19]=4[S:18]3(=[O:30])=[O:29])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+].C(=O)([O-])O.[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[CH2:23][CH2:22][CH:21]([OH:24])[C:20]4[N:25]([CH3:28])[CH:26]=[CH:27][C:19]=4[S:18]3(=[O:30])=[O:29])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 9889134HCID 9889134, compound

Product 1

HCID 9910903HCID 9910903, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 240 mg (0.57 mmol) of Compound 23 in 5 ml of ethanol, 200 mg (5.3 mmol) of sodium borohydride were added gradually under ice-cooled stirring. The resulting mixture was stirred under ice cooling for 1 hour and further at room temperature for 4 hours. A saturated aqueous solution of ammonium chloride was added to the reaction mixture under ice cooling, followed by the addition of a saturated aqueous solution of sodium hydrogencarbonate so that the mixture was alkalinized. The water layer was extracted with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (eluent: methanol/methylene chloride=1/20), whereby 186 mg of the title compound were obtained (yield: 77%).

Workup

  1. additionwere added gradually under ice-
  2. temperaturecooled
  3. stirringThe resulting mixture was stirred under ice cooling for 1 hour and further at room temperature for 4 hours
  4. extractionThe water layer was extracted with methylene chloride
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column (eluent: methanol/methylene chloride=1/20)

Sources & evidence

ORD record
ord-4838391431ca41f8919ffbd385d1349a
Source dataset
uspto-grants-2001_08
Patent number
US06271223B1

Reaction notes

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