Ammonium Chloride → HCID 58424901, compound

HRID 2409450Notes

Reaction equation

HRID 2409450 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[C:22]2[C:21]3[NH:20][CH2:19][CH2:18][CH2:17][C:16]=3[C:15](=[O:23])[N:14]([CH2:24][O:25][CH3:26])[C:13]=2[CH:12]=[C:11]([C:27](OCC)=[O:28])[CH:10]=1.[Cl-].[NH4+]>O1CCCC1>[OH:28][CH2:27][C:11]1[CH:10]=[C:9]([O:8][CH3:7])[C:22]2[C:21]3[NH:20][CH2:19][CH2:18][CH2:17][C:16]=3[C:15](=[O:23])[N:14]([CH2:24][O:25][CH3:26])[C:13]=2[CH:12]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 58424908HCID 58424908, compound

Product 1

HCID 58424901HCID 58424901, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Tetrahydrofuran (10.0 ml) was added to lithium aluminum hydride (125 mg, 3.30 mmol) and cooled to 0° C. The compound (457 mg, 1.32 mmol) prepared in step 7 was dissolved in tetrahydrofuran (10.0 ml) was added dropwise slowly at 0° C. and the resulting mixture was stirred at the same temperature for 1 hour. After completion, ammonium chloride aqueous solution was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated to dryness. The residue was then purified by flash column chromatography (dichloromethane:methanol=10:1) to obtain the title compound (399 mg, yield: 99.2%, ivory solid).

Workup

  1. additionwas added dropwise slowly at 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue was then purified by flash column chromatography (dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-ea3aab219296417e8d60c878a4b860a9
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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