Sodium Hydroxide → HCID 9868197, compound

HRID 323596Notes

Reaction equation

HRID 323596 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, 10 H); 6.75 (bd, J=8.2 Hz, 2 H); 6.26 (bs, 8 H); 5.91 (t, J=6.6 Hz, 1 H); 4.02 (t, J=6.2 Hz, 2 H); 3.76 (m, 1 H); 3.59 (m)+3.31 (m), 2 H; 3.07 (bs (4 H); 2.70-2.95 (m, 4 H); 2.51 (bq, 2 H); 1.66 (bm, 6 H); 1.03 (t, J=7.2 Hz, 3 H).

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-99cc91daf86947b5b4c7c652d6b496f3
Source dataset
uspto-grants-2001_04
Patent number
US06214820B1

Reaction notes

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