Ammonium Chloride → HCID 10690868, compound

HRID 1955120Notes

Reaction equation

HRID 1955120 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 lmL 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) δ7.74, 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-74ff729c886442b1bb64e7b136718182
Source dataset
uspto-grants-2000_09
Patent number
US06124334

Reaction notes

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