Sodium Hydroxide → HCID 9868197, compound

HRID 1067868Notes

Reaction equation

HRID 1067868 reaction equation
C([O:3][C:4](=[O:35])[CH:5]([O:32][CH2:33][CH3:34])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][O:16][CH:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][CH2:20][C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]2=3)=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C>[CH:28]1[C:19]2[CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH:17]([O:16][CH2:15][CH2:14][O:13][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][CH:5]([O:32][CH2:33][CH3:34])[C:4]([OH:35])=[O:3])=[CH:12][CH:11]=3)[C:18]=2[CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9804941HCID 9804941, compound

Product 1

HCID 9868197HCID 9868197, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(4-[2-( 10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-yloxy)-ethoxy]-phenyl)-2-ethoxy-propanoic acid ethyl ester (example 8) (1.5 g, 3.2 mmol) was dissolved in ethanol (30 ml) and 20% sodium hydroxide (3 ml) was added. After 3 days ethanol was evaporated in vacuo, water (50 ml) and hydrochloric 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 (1.1 g, 78%) was dissolved in ethanol and treated with (L)-lysine monohydrate (0.41 g). Ethanol was evaporated and the residue triturated with diethyl ether. The crystalline product was filtered off and dried in the air. This afforded 1.45 g of the title compound as salt with (L)-lysine (dihydrate). M.p. 148-150° C. 1H NMR (250 MHz, DMSO-d6 δ7.00-7.35 (m, 10H); 6.75 (bd, J=8.2 Hz, 2H); 6.26 (bs, 8H); 5.91 (t, J=6.6 Hz, 1H); 4.02 (t, J=6.2 Hz, 2H); 3.76 (m, 1H); 3.59 (m) +3.31 (m), 2 H; 3.07 (bs (4H); 2.70-2.95 (m, 4H); 2.51 (bq, 2H); 1.66 (bm, 6H); 1.03 (t, J=7.2 Hz, 3H).

Workup

  1. customAfter 3 days ethanol was evaporated in vacuo, water (50 ml) and hydrochloric 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 (1.1 g, 78%) was dissolved in ethanol
  7. additiontreated with (L)-lysine monohydrate (0.41 g)
  8. customEthanol was evaporated
  9. customthe residue triturated with diethyl ether
  10. filtrationThe crystalline product was filtered off
  11. customdried in the air

Sources & evidence

ORD record
ord-d0ec203ca6a040b8b536dbb4374e7d1f
Source dataset
uspto-grants-2001_06
Patent number
US06248781B1

Reaction notes

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