Sodium Hydroxide → 4-[8-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]butanoic acid

HRID 1514267Notes

Reaction equation

HRID 1514267 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:37]=[CH:36][C:22]4[CH2:23][N:24]([CH2:28][CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])[CH2:25][CH2:26][O:27][C:21]=4[CH:20]=3)[N:15]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12]>C(O)C>[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:37]=[CH:36][C:22]4[CH2:23][N:24]([CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[CH2:25][CH2:26][O:27][C:21]=4[CH:20]=3)[N:15]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59403500Ethyl 4-[8-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]butanoate

Product 1

HCID 441288234-[8-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]butanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2M Sodium hydroxide (aq) (0.5 ml, 1.000 mmol) was added to a solution of ethyl 4-[8-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]butanoate (Preparation 36) (0.103 g, 0.206 mmol) in ethanol (4 ml) and left at room temperature for 2 hours. The reaction mixture was evaporated and the residue dissolved in water/EtOAc (30 ml of each) and acidified with acetic acid. The organic layer was collected, dried (magnesium sulphate), evaporated and azeotroped with 15 ml of toluene. The title compound was obtained by triturating with ether and filtering off as a white solid (65 mg). δH (400 MHz, d6DMSO) 1.36 (6H, d), 1.70 (2H, m), 2.23 (2H, t), 2.33 (2H, t), 3.02 (2H, m), 3.84 (2H, s), 4.06 (2H, m), 4.89 (1H, m), 7.44 (2H, m), 7.61 (1H, d), 7.72 (1H, dd), 8.10 (1H, dd), 8.18 (1H, d); MS (ES) C24H2635ClN3O5 requires 471; found 472 [M+H]+.

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue dissolved in water/EtOAc (30 ml of each) and
  3. customThe organic layer was collected
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated
  6. customazeotroped with 15 ml of toluene

Sources & evidence

ORD record
ord-2b56f6dc4b224fcc890c123a702b1eff
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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