Sodium Hydroxide → HCID 44128984, compound

HRID 1514276Notes

Reaction equation

HRID 1514276 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:32]=[CH:31][C:19]4[CH2:20][CH2:21][N:22]([CH2:25][C:26]([O:28]CC)=[O:27])[CH2:23][CH2:24][C:18]=4[CH:17]=3)[N:12]=2)=[CH:7][C:6]=1[C:33]([F:36])([F:35])[F:34])[CH3:3].[OH-].[Na+]>C(O)C>[CH3:3][CH:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:32]=[CH:31][C:19]4[CH2:20][CH2:21][N:22]([CH2:25][C:26]([OH:28])=[O:27])[CH2:23][CH2:24][C:18]=4[CH:17]=3)[N:12]=2)=[CH:7][C:6]=1[C:33]([F:36])([F:35])[F:34])[CH3:1]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59403505HCID 59403505, compound

Product 1

HCID 44128984HCID 44128984, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of ethyl (7-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)acetate (Preparation 48) (59 mg, 0.12 mmol), aqueous sodium hydroxide (2M, 590 μL, 1.18 mmol) and ethanol (6 ml) was heated at 40° C. for 1 hr. The reaction mixture was cooled to room temperature and concentrated. The residue was taken up in water, which was then acidified to pH 6 with acetic acid. The aqueous phase was extracted with EtOAc (2×20 ml) before the combined organic fractions were concentrated and the residue was triturated with EtOAc and the title compound was filtered off and dried in a vacuum oven to give a white solid (36 mg, 0.08 mmol). δH (d6DMSO, 400 MHz): 8.41 (1H, dd), 8.30 (1H, d), 7.88-7.82 (2H, m), 7.58 (1H, d), 7.35 (1H, d), 4.98 (1H, septet), 3.25 (2H, s), 3.06-2.96 (4H, m), 2.89-2.81 (4H, m), 1.36 (6H, d); MS (ES−): C24H24F3N3O4 requires 475; found 474 [M−H+].

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. extractionThe aqueous phase was extracted with EtOAc (2×20 ml) before the combined organic fractions
  4. concentrationwere concentrated
  5. customthe residue was triturated with EtOAc
  6. filtrationthe title compound was filtered off
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-fa89ee0496314df28df39e9e7cb61376
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

Loading…