Sodium borohydride → HCID 11774705, compound

HRID 1855219Notes

Reaction equation

HRID 1855219 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>[O:23]1[C:19]2[CH:18]=[C:17]([C:14]3([C:12]([NH:11][C:9]4[S:10][C:6]([CH:4]([C:3]5[CH:26]=[CH:27][CH:28]=[CH:29][C:2]=5[Cl:1])[OH:5])=[CH:7][N:8]=4)=[O:13])[CH2:16][CH2:15]3)[CH:25]=[CH:24][C:20]=2[O:21][CH2:22]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%). 1H NMR (400 MHz, DMSO-d6) δ 1.10-1.14 (m, 2H), 1.41-1.45 (m, 2H), 6.00 (s, 2H), 6.14 (s, 1H), 6.86 (d, J=1.0 Hz, 2H), 6.95 (t, J=1.0 Hz, 1H), 7.14 (d, J=0.6 Hz, 1H), 7.29-7.34 (m, 1H), 7.38-7.43 (m, 2H), 7.71 (d, J=7.5 Hz, 1H), 10.93 (s, 1H) 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-d1fdad47122347e0847beac3d5018d7e
Source dataset
uspto-grants-2015_02
Patent number
US08962856B2

Reaction notes

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