Water → HCID 68470289, compound

HRID 1514259Notes

Reaction equation

HRID 1514259 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[CH2:27][N:26]([CH2:28][CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])[CH2:25][CH2:24][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+].O.CCOCC>C(O)C>[C:31]([OH:33])(=[O:32])[CH3:30].[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[CH2:27][N:26]([CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[CH2:25][CH2:24][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

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 14798Sodium Hydroxide2×HCID 59403477HCID 59403477, compound

Product 1

HCID 68470289HCID 68470289, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-[7-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl]butanoate (preparation 11) (90 mg, 0.184 mmol) dissolved in ethanol (20 ml) was treated with sodium hydroxide (0.184 ml, 0.368 mmol) (2N (aq)) solution followed by water (5.00 ml). This mixture was stirred at RT for 3 hours and left standing overnight. 2N NaOH (aq) (150 p1) was added and the reaction mixture stirred for 3 hours. Then ethanol was removed by evaporation and the aqueous layer acidified using AcOH. The product was extracted into EtOAc (50 ml) and dried over MgSO4. Solvent removal by evaporation yielded a white precipitate. Ether was added and the solid filtered off and washed with ether to yield the title compound (44 mg) on drying. δH (400 MHz, d6DMSO) 1.39 (6H, d), 1.91-1.95 (4H, m), 2.30 (2H, t), 2.96 (2H, m), 3.13 (2H, m), 3.53 (2H, m), 4.60 (2H, s), 4.94-5.03 (1H, m), 7.57 (1H, d), 7.68 (1H, d), 7.97-8.00 (2H, m), 8.41 (1H, dd), 8.52 (1H, d) 10.6 (1H, v. broad s), 12.3 (1H, v. broad s); MS (ES) C26H28N4O4 requires 460; found 461.0 [M+H]+.

Workup

  1. waitleft
  2. waitstanding overnight
  3. stirringthe reaction mixture stirred for 3 hours
  4. customThen ethanol was removed by evaporation
  5. extractionThe product was extracted into EtOAc (50 ml)
  6. dry with materialdried over MgSO4
  7. customSolvent removal
  8. customby evaporation
  9. customyielded a white precipitate
  10. filtrationthe solid filtered off
  11. washwashed with ether

Sources & evidence

ORD record
ord-95dc1380cbf743e0ad29e46aaa9df7da
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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