Sodium Hydroxide → HCID 68467752, compound

HRID 1514266Notes

Reaction equation

HRID 1514266 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:36]=[CH:35][C:22]4[CH2:23][N:24]([CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])[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>[ClH:3].[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:36]=[CH:35][C:22]4[CH2:23][N:24]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[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 59403499Ethyl 3-[8-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]propanoate

Product 1

HCID 68467752HCID 68467752, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2M Sodium hydroxide solution (aq) (0.5 ml, 1.000 mmol) was added to a solution of ethyl 3-[8-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]propanoate (Preparation 35) (0.09 g, 0.185 mmol) in ethanol (4 ml) and left at room temperature for 2 hours. The reaction was then evaporated and the resulting crude dissolved in EtOAc/water (30 ml of each) and acidified with acetic acid. The organic layer was dried (magnesium sulphate) and evaporated. The resulting crude was azeotroped with 20 ml of toluene and the residue dissolved in 10 ml of DCM. 1M HCl (1 ml) in ether was added, the reaction mixture evaporated then triturated with ether. The title compound (56 mg) was filtered off as an off-white solid hydrochloride salt. 6H (400 MHz, MeOD) 1.42 (6H, d), 2.92 (2H, t), 3.55 (2H, t), 3.78 (2H, m), 4.40 (2H, m), 4.65 (2H, s), 4.87 (1H, m), 7.31 (1H, d), 7.61 (1H, d), 7.87 (1H, d), 7.96 (1H, dd), 8.11 (1H, dd), 8.21 (1H, d); MS (ES) C23H2435ClN3O6 requires 457; found 458 [M+H]+.

Workup

  1. customThe reaction was then evaporated
  2. dissolutionthe resulting crude dissolved in EtOAc/water (30 ml of each) and
  3. dry with materialThe organic layer was dried (magnesium sulphate)
  4. customevaporated
  5. customThe resulting crude was azeotroped with 20 ml of toluene
  6. dissolutionthe residue dissolved in 10 ml of DCM
  7. addition1M HCl (1 ml) in ether was added
  8. customthe reaction mixture evaporated
  9. customthen triturated with ether
  10. filtrationThe title compound (56 mg) was filtered off as an off-white solid hydrochloride salt

Sources & evidence

ORD record
ord-b2a936b7eb8a4f59aeade6aababd2def
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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