Ethanol → HCID 86660099, compound

HRID 1951902Notes

Reaction equation

HRID 1951902 reaction equation
[BH4-].[Na+].C(O)C.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2([CH3:28])[C:17]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([F:25])[CH:19]=3)=[N:16][S:15](=[O:27])(=[O:26])[NH:14]2)=[CH:9][N:8]=1>C(OCC)(=O)C>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C@:13]2([CH3:28])[C@H:17]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([F:25])[CH:19]=3)[NH:16][S:15](=[O:26])(=[O:27])[NH:14]2)=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 58542319HCID 58542319, compound

Product 1

HCID 86660099HCID 86660099, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (1.00 g, 26.4 mmol) was gradually added to an ethanol (63 ml) solution of the compound (7.13 g, 19.1 mmol) obtained in Step 7 above under ice cooling and the resulting mixture was stirred at the same temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and then the residue obtained was diluted with ethyl acetate, washed with 1 N aqueous hydrochloric acid solution and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography [n-hexane:ethyl acetate=1:2 (v/v)] to give the title compound (4.36 g, 59%) as a pale yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue obtained
  3. washwashed with 1 N aqueous hydrochloric acid solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography [n-hexane:ethyl acetate=1:2 (v/v)]

Sources & evidence

ORD record
ord-8d6303b0359e47f7896ea9a222a2f864
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

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