Sodium borohydride → HCID 58504204, compound

HRID 2407705Notes

Reaction equation

HRID 2407705 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]1[C:15]([C:16](OC)=[O:17])=[CH:14][C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[OH:17][CH2:16][C:15]1[N:11]([CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[N:12]=[C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 58503993HCID 58503993, compound

Product 1

HCID 58504204HCID 58504204, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound prepared in Example 121 (0.620 g) was suspended in methanol (30 mL) and sodium borohydride (0.088 g) was added portion-wise to the stirred reaction mixture at room temperature. Excess sodium borohydride was added portion-wise to the reaction mixture and the system heated at reflux overnight. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The solids were partitioned between saturated aqueous ammonium chloride and ethyl acetate. The organics were washed with brine, dried, magnesium sulfate and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography (pre-absorbed to silica) (eluant: 50-75% ethyl acetate/hexane 0.5% triethylamine) to furnish the title compound (0.253 g) having the following physical data.

Workup

  1. customto the stirred reaction mixture at room temperature
  2. temperaturethe system heated
  3. temperatureat reflux overnight
  4. concentrationconcentrated under reduced pressure
  5. customThe solids were partitioned between saturated aqueous ammonium chloride and ethyl acetate
  6. washThe organics were washed with brine
  7. customdried
  8. concentrationmagnesium sulfate and concentrated under reduced pressure
  9. customto afford the crude material, which
  10. customwas purified by flash column chromatography (pre-absorbed to silica) (eluant: 50-75% ethyl acetate/hexane 0.5% triethylamine)

Sources & evidence

ORD record
ord-de65650bf8db4593ae14d5cc66133147
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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