Ammonium Chloride → HCID 10690868, compound

HRID 1415907Notes

Reaction equation

HRID 1415907 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:20]2[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]2=[O:30])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15](OCC)=[O:16])=[CH:9]1.[BH4-].[Li+].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([N:20]2[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]2=[O:30])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][OH:16])=[CH:9]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 10740673HCID 10740673, compound

Product 1

HCID 10690868HCID 10690868, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 275 mg (0.66 mmol) of the compound of Example 24 in 15 mL THF was treated with 287 mg (13.2 mmol) of lithium borohydride followed by stirring at ambient temperature for 18 h. The solution was treated with 1 mL of saturated ammonium chloride solution, diluted with ethyl acetate, and extracted with water (3×). Drying (Na2SO4) and concentration in vacuo afforded an oil, which was chromatographed over 20 g of 230-400 mesh silica gel eluting with 2-4% (v/v) methanol in dichloromethane. These procedures afforded 96 mg (39%) of the title compound as a white solid. 1H NMR (CDCl3) δ 7.74, 7.66, 7.38, 7.27, 7.18, 6.95, 6.61, 5.98, 4.82, 4.37, 4.27, 4.09, 3.83, 3.68, 2.88, 2.82, 2.62, 2.04, 1.79.

Workup

  1. extractionextracted with water (3×)
  2. customDrying
  3. concentration(Na2SO4) and concentration in vacuo
  4. customafforded an oil, which
  5. customwas chromatographed over 20 g of 230-400 mesh silica gel eluting with 2-4% (v/v) methanol in dichloromethane

Sources & evidence

ORD record
ord-b41fe1f9d781422695ec8f416d1e959c
Source dataset
uspto-grants-1999_06
Patent number
US05910504

Reaction notes

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