Sodium Hydroxide → HCID 44129145, compound

HRID 1514285Notes

Reaction equation

HRID 1514285 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][CH2:30][C:31]([O:33]CC)=[O:32])[CH2:23][C:22]=4[CH:36]=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][CH2:30][C:31]([OH:33])=[O:32])[CH2:23][C:22]=4[CH:36]=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 68466841HCID 68466841, compound

Product 1

HCID 44129145HCID 44129145, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-[7-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]butanoate (Preparation 80) (0.084 g, 0.171 mmol) was dissolved in Ethanol (2 ml). Then 2N NaOH (1 ml, 2.000 mmol) was added and the reaction left standing at RT for 3 hours. Ethanol was removed by evaporation and the resulting residue dissolved in EtOAc and water, acidified with acetic acid and the phases separated. The organic phase was dried (MgSO4), evaporated and triturated with ether. Drying under vacuum overnight at 50° C. yielded the title compound (22 mg) as a white solid. δH (d6DMSO, 400 MHz): 1.37 (6H, d), 1.66 (2H, t), 2.22 (2H, t), 2.45 (2H, m), 3.01 (2H, m), 3.82 (2H, s), 4.07 (2H, m), 4.95 (1H, m), 7.14 (1H, d), 7.54 (1H, d), 7.89 (1H, dd), 7.96 (1H, d), 8.38 (1H, dd), 8.50 (1H, d); MS (ES): C25H26N4O5 requires 462; found 463 [M+H]+.

Workup

  1. waitthe reaction left
  2. customEthanol was removed by evaporation
  3. dissolutionthe resulting residue dissolved in EtOAc
  4. customthe phases separated
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated
  7. customtriturated with ether
  8. customDrying under vacuum overnight at 50° C.

Sources & evidence

ORD record
ord-709db54ef2dd4e7eb5074f36e8214e3f
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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