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

HRID 1514286Notes

Reaction equation

HRID 1514286 reaction equation
[OH-].[Na+].[C:3]([C:5]1[CH:6]=[C:7]([C:15]2[O:19][N:18]=[C:17]([C:20]3[C:30]4[O:29][CH2:28][CH2:27][N:26]([CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37]CC)=[O:36])[CH2:25][C:24]=4[CH:23]=[CH:22][CH:21]=3)[N:16]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])#[N:4]>C(O)C>[C:3]([C:5]1[CH:6]=[C:7]([C:15]2[O:19][N:18]=[C:17]([C:20]3[C:30]4[O:29][CH2:28][CH2:27][N:26]([CH2:31][CH2:32][CH2:33][CH2:34][C:35]([OH:37])=[O:36])[CH2:25][C:24]=4[CH:23]=[CH:22][CH:21]=3)[N:16]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])#[N:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59403540Ethyl 5-[9-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]pentanoate

Product 1

HCID 441292205-[9-(5-{3-Cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]pentanoic acidYield 30.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

2M sodium hydroxide (0.347 mL, 0.694 mmol) was added to a stirred solution of ethyl 5-[9-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]pentanoate (Preparation 93) (70 mg, 0.139 mmol) in ethanol (5 mL) and the mixture was heated to 60° C. overnight. The reaction mixture was allowed to cool to room temperature and the solvent evaporated. The residue was diluted with water, acidified with 2M hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water, dried and evaporated to give the product as an off white solid (20 mg).

Workup

  1. temperatureto cool to room temperature
  2. customthe solvent evaporated
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-48cf665a506843c4855abd3e2bf89e9a
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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