Sodium Hydroxide → HCID 69944314, compound

HRID 1934663Notes

Reaction equation

HRID 1934663 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:22][C@H:23]([CH3:26])[CH2:24][OH:25])=[C:7]([CH:21]=1)[C:8]([NH:10][CH2:11][C:12]1[CH:20]=[CH:19][C:15]2[O:16][CH2:17][O:18][C:14]=2[CH:13]=1)=[O:9])#[N:2].[OH-:27].[Na+]>C(O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:22][C@H:23]([CH3:26])[CH2:24][OH:25])=[C:7]([CH:21]=1)[C:8]([NH:10][CH2:11][C:12]1[CH:20]=[CH:19][C:15]2[O:16][CH2:17][O:18][C:14]=2[CH:13]=1)=[O:9])(=[O:27])[NH2:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53815966HCID 53815966, compound

Product 1

HCID 69944314HCID 69944314, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (R)-5-cyano-2-(2-hydroxy-1-methylethylamino)-N-(1,3-benzodioxol-5-ylmethyl)benzamide (76 mg) in ethanol (6 mL) was added 1N-sodium hydroxide (0.65 mL), and the mixture was heated for 6 hours under reflux. The solvent was evaporated in vacuo. The residue was diluted with ethyl acetate and washed successively with water and brine. The organic layer was dried over sodium sulfate and evaporated in vacuo. The residue was subjected to a silica gel column chromatography eluting with a mixture of chloroform and methanol (9:1) to give (R)-5-carbamoyl-2-(2-hydroxy-1-methylethylamino)-N-(1,3-benzodioxol-5-ylmethyl)benzamide (27 mg) as a solid substance.

Workup

  1. temperaturethe mixture was heated for 6 hours
  2. temperatureunder reflux
  3. customThe solvent was evaporated in vacuo
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed successively with water and brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customevaporated in vacuo
  8. washeluting with a mixture of chloroform and methanol (9:1)

Sources & evidence

ORD record
ord-dc286e67ce464520a8a9411457f796b0
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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