Sodium Hydroxide → (2R)-2-Methyloxirane-2-carboxylicacid-(4-cyano-3-methylphenyl)amide

HRID 1888364Notes

Reaction equation

HRID 1888364 reaction equation
Br[CH2:2][C@@:3]([OH:17])([CH3:16])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([CH3:15])[CH:8]=1)=[O:5].[OH-].[Na+]>C1(C)C=CC=CC=1>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([NH:6][C:4]([C@@:3]2([CH3:16])[CH2:2][O:17]2)=[O:5])=[CH:8][C:9]=1[CH3:15])#[N:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57587072(2R)-3-Bromo-2-hydroxy-2-methyl-N-(4-cyano-3-methylphenyl)propion-amide

Product 1

HCID 86761994(2R)-2-Methyloxirane-2-carboxylicacid-(4-cyano-3-methylphenyl)amideYield 80.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(2R)-3-Bromo-2-hydroxy-2-methyl-N-(4-cyano-3-methylphenyl)propion-amide (1.54 g, 5.2 mmol) was dissolved in 50 ml of toluene and stirred for 5 minutes with 15 ml of 1 M NaOH at room temperature. Organic layer was separated and washed with 2×25 ml of water. Toluene was filtered and evaporated to give 0.905 g of the product.

Workup

  1. customOrganic layer was separated
  2. washwashed with 2×25 ml of water
  3. filtrationToluene was filtered
  4. customevaporated

Sources & evidence

ORD record
ord-86aca3b7271844cf90dbb314ecc37f36
Source dataset
uspto-grants-2013_08
Patent number
US08501814B2

Reaction notes

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