Sodium Hydroxide → HCID 44129143, compound

HRID 1514284Notes

Reaction equation

HRID 1514284 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]4[O:27][CH2:26][CH2:25][N:24]([CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])[CH2:23][C:22]=4[CH:35]=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[CH:19]=[CH:20][C:21]4[O:27][CH2:26][CH2:25][N:24]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH2:23][C:22]=4[CH:35]=3)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:11])[CH3:12])#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68467368HCID 68467368, compound

Product 1

HCID 44129143HCID 44129143, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-[7-(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 78) (0.092 g, 0.193 mmol) was dissolved in Ethanol (2 ml). Then 2N NaOH (1 ml, 2.000 mmol) was added and the reaction mixture left standing at RT for 2 hours. Ethanol was removed by evaporation and the resulting residue dissolved in EtOAc and water, acidified with acetic acid and the layers separated. Solid separated from the aqueous phase and was filtered off solid and dried under vacuum overnight at 50° C. to give the title compound (8 mg) as a white solid. δH (d6DMSO, 400 MHz): 1.37 (6H, d), 2.38 (2H, t), 2.67 (2H, m), 3.03 (2H, m), 3.89 (2H, s), 4.07 (2H, m), 4.97 (1H, m), 7.14 (1H, d), 7.54 (1H, d), 7.89 (1H, dd), 7.98 (1H, d), 8.39 (1H, dd), 8.51 (1H, d); MS (ES): C24H24N4O5 requires 448; found 449 [M+H]+.

Workup

  1. waitthe reaction mixture left
  2. customEthanol was removed by evaporation
  3. dissolutionthe resulting residue dissolved in EtOAc
  4. customthe layers separated
  5. customSolid separated from the aqueous phase
  6. filtrationwas filtered off solid
  7. customdried under vacuum overnight at 50° C.

Sources & evidence

ORD record
ord-7b9be29eb620423e898515e4cf8d8806
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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