Sodium Hydroxide → 3-[9-(5-{3-Cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]propanoic acid

HRID 1514288Notes

Reaction equation

HRID 1514288 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[C:28]4[O:27][CH2:26][CH2:25][N:24]([CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])[CH2:23][C:22]=4[CH:21]=[CH:20][CH:19]=3)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].[OH-].[Na+]>C(O)C>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[C:28]4[O:27][CH2:26][CH2:25][N:24]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])[CH2:23][C:22]=4[CH:21]=[CH:20][CH:19]=3)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59403543Ethyl 3-[9-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]propanoate

Product 1

HCID 441292233-[9-(5-{3-Cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]propanoic acidYield 42.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 3-[9-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]propanoate (Preparation 92) (40 mg, 0.084 mmol) was dissolved in ethanol (5 ml). 2M sodium hydroxide (0.210 ml, 0.420 mmol) was added and the reaction mixture stirred at 60° C. for 4 hours. The solvent was evaporated, then the reaction mixture was diluted with water, neutralised with 2M hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water, dried and evaporated to give the product as a colourless solid (16 mg).

Workup

  1. customThe solvent was evaporated
  2. additionthe reaction mixture was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-930decb32f0d47748dc107d14b2d6f52
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

Loading…