Ammonium Chloride → HCID 10740673, compound

HRID 1415906Notes

Reaction equation

HRID 1415906 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]([CH:13]=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9]1.[BH4-].[Na+].[Cl-].[NH4+]>Cl[Cu].CO.C1COCC1>[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]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 54360958HCID 54360958, compound

Product 1

HCID 10740673HCID 10740673, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 150 mg (0.36 mmol) of the compound of Example 23 and 54 mg (0.54 mmol) of copper [I] chloride in 15 mL 1:1 Methanol-THF at 0° C. was treated with 136 mg (3.6 mmol) of sodium borohydride. The solution was stirred at 0° C. for 30 min and then warmed to ambient temperature for 1 h. The solution was treated with 2 mL saturated ammonium chloride solution, followed by filtration through celite. The filtrate was concentrated in vacuo and the residue was diluted with ethyl acetate and extracted with water (3×). Drying (Na2SO4) and concentration in vacuo afforded 150 mg (99%) of the title compound as a white solid. 1H NMR (CDCl3) δ 7.60, 7.34, 7.33, 6.91, 6.81, 6.21, 5.97, 4.81, 4.15, 4.08, 3.82, 3.72, 3.65, 2.87, 2.62, 2.04, 1.26.

Workup

  1. temperaturewarmed to ambient temperature for 1 h
  2. filtrationfollowed by filtration through celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. additionthe residue was diluted with ethyl acetate
  5. extractionextracted with water (3×)
  6. customDrying
  7. concentration(Na2SO4) and concentration in vacuo

Sources & evidence

ORD record
ord-18c4e83d7a97438fa694523cb1bd209d
Source dataset
uspto-grants-1999_06
Patent number
US05910504

Reaction notes

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