Ammonium Chloride → HCID 59897692, compound

HRID 1841624Notes

Reaction equation

HRID 1841624 reaction equation
[Br-].[Li+].B.[Na].C([O:12][C:13]([C@@H:15]([NH:29][C:30]([N:32]([CH2:38][CH2:39][N:40]([CH3:42])[CH3:41])[CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])=[O:31])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][CH:18]=1)=O)C1C=CC=CC=1.[Cl-].[NH4+]>C(O)C>[C:20]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:19]=[CH:18][C:17]([CH2:16][C@H:15]([NH:29][C:30]([N:32]([CH2:38][CH2:39][N:40]([CH3:41])[CH3:42])[CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])=[O:31])[CH2:13][OH:12])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 82050Lithium BromideHCID 59897690HCID 59897690, compound2×HCID 178418435HCID 178418435, compound

Product 1

HCID 59897692HCID 59897692, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Lithium bromide (179 mg) and sodium boron hydride (52 mg) were suspended in anhydrous ethanol (1 ml) in the nitrogen gas atmosphere and the resulting suspension was stirred at room temperature for one hour. To the suspension, there was dropwise added a solution of 1-[(1S)-1-(benzyloxycarbonyl)-2-(4-biphenylyl) ethyl]-3-[2-(dimethylamino)ethyl]-3-isopentyl urea (Compound 4-1, 310 mg) in anhydrous ethanol (5.8 ml) with ice cooling. The resulting mixture was stirred at room temperature for 24 hours. Saturated ammonium chloride aqueous solution was added to the reaction liquid with ice cooling and then the resulting mixture was extracted with ether. The resulting organic phase was washed with saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting oily product was purified through the silica gel column chromatography to give the title compound (Compound 5-1, 138 mg).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 24 hours
  2. extractionthe resulting mixture was extracted with ether
  3. washThe resulting organic phase was washed with saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting oily product was purified through the silica gel column chromatography

Sources & evidence

ORD record
ord-9b05234f29ed4a2e83dbb2987cc7beef
Source dataset
uspto-grants-2004_01
Patent number
US06683200B2

Reaction notes

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