Sodium Hydroxide → 3-(4-[2-([10,11-dihydro-5H-dibenzo[a,d]cycloh epten-5-yi]-methyl-amino)-ethoxy]-phenyl)-2-ethoxypropanoic acid

HRID 1060858Notes

Reaction equation

HRID 1060858 reaction equation
C([O:3][C:4](=[O:36])[CH:5]([O:33][CH2:34][CH3:35])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][N:16]([CH:18]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[CH2:22][CH2:21][C:20]3[CH:29]=[CH:30][CH:31]=[CH:32][C:19]2=3)[CH3:17])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C>[CH:29]1[C:20]2[CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH:18]([N:16]([CH3:17])[CH2:15][CH2:14][O:13][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][CH:5]([O:33][CH2:34][CH3:35])[C:4]([OH:36])=[O:3])=[CH:12][CH:11]=3)[C:19]=2[CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 98700773-(4-[2-([10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl]-methyl-amino)-ethoxy]-phenyl)-2-ethoxypropanoic acid ethyl ester

Product 1

HCID 98688363-(4-[2-([10,11-dihydro-5H-dibenzo[a,d]cycloh epten-5-yi]-methyl-amino)-ethoxy]-phenyl)-2-ethoxypropanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(4-[2-([10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl]-methyl-amino)-ethoxy]-phenyl)-2-ethoxypropanoic acid ethyl ester (example 10)(1.5 g, 3.07 mmol) was dissolved in ethanol (20 ml) and 20% sodium hydroxide (2 ml) was added. After 6 days ethanol was evaporated in vacuo, water (50 ml) and acetic acid (2 ml) were added and the mixture was extracted with dichloromethane. The organic phase was dried (MgSO4) and the solvent evaporated in vacuo. The residue (1.4 g) was dissolved in acetone and neutralized with solution of hydrogen chloride in diethyl ether. The solvents were evaporated and the residue was triturated with diethyl ether yielding 1.15 g (74%) of the title compound as amorphous solid (hemihydrate). 1H NMR (250 MHz, DMSO-d6) δ10.50 (bs, 1 H); 7.60 (bs)+7.10-7.50 (m, 10 H), 6.87 (d, J=7.9 Hz, 2 H), 5.84 (bd, J=7.0 Hz, 1 H), 4.49 (bs, 2 H), 4.00 (t, J=5.6 Hz; +bm, 3 H), 3.30-3,60 (m+m, 4 H), 2.80-3.10 (s+bm, 7 H), 1.07 (t, J=7.2 Hz, 3 H).

Workup

  1. customAfter 6 days ethanol was evaporated in vacuo, water (50 ml) and acetic acid (2 ml)
  2. additionwere added
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customthe solvent evaporated in vacuo
  6. dissolutionThe residue (1.4 g) was dissolved in acetone and neutralized with solution of hydrogen chloride in diethyl ether
  7. customThe solvents were evaporated
  8. customthe residue was triturated with diethyl ether yielding 1.15 g (74%) of the title compound as amorphous solid (hemihydrate)

Sources & evidence

ORD record
ord-053c530fc5ac477a95b1c7c29f3997a2
Source dataset
uspto-grants-2003_02
Patent number
US06525086B2

Reaction notes

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