Sodium borohydride → HCID 11774705, compound

HRID 408500Notes

Reaction equation

HRID 408500 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[C:4]([C:6]1[S:10][C:9]([NH:11][C:12]([C:14]2([C:17]3[CH:25]=[CH:24][C:20]4[O:21][CH2:22][O:23][C:19]=4[CH:18]=3)[CH2:16][CH2:15]2)=[O:13])=[N:8][CH:7]=1)=[O:5].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH:4]([OH:5])[C:6]1[S:10][C:9]([NH:11][C:12]([C:14]2([C:17]3[CH:25]=[CH:24][C:20]4[O:21][CH2:22][O:23][C:19]=4[CH:18]=3)[CH2:15][CH2:16]2)=[O:13])=[N:8][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58609757HCID 58609757, compound

Product 1

HCID 11774705HCID 11774705, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Benzo[1,3]dioxol-5-yl-cyclopropanecarboxylic acid [5-(2-chloro-benzoyl)-thiazol-2-yl]-amide (1.0 g, 2.3 mmol) was suspended in 150 mL of anhydrous methanol. Sodium borohydride (1.3 g, 35 mmol) was slowly added and the resulting pale yellow solution was allowed to stir for 1 hour at room temperature. The crude product was evaporated to dryness and then dissolved in a minimum of ethyl acetate. The organic was washed three times with an equal volume of 1N hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride. The organic layer was then dried over sodium sulfate, filtered, and evaporated to dryness to yield the product as a beige solid (0.64 g, 1.5 mmol, 63%) ESI-MS m/z calc. 428.1. found; 429.5 (M+1)+ Retention time 3.17 minutes.

Workup

  1. customThe crude product was evaporated to dryness
  2. dissolutiondissolved in a minimum of ethyl acetate
  3. washThe organic was washed three times with an equal volume of 1N hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride
  4. dry with materialThe organic layer was then dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-109530e8ba7940dc92d4b065659ddce4
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Reaction notes

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