Sodium Hydroxide → 3-(4-[2-(6,11-Dihydrodibenzo[b,e]thiepin-11-yloxy)-ethoxy]-phenyl)-2-ethoxy-propionic acid

HRID 1060847Notes

Reaction equation

HRID 1060847 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][S: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:31]1[C:18]2[CH:17]([O:16][CH2:15][CH2:14][O:13][C:10]3[CH:11]=[CH:12][C:7]([CH2:6][CH:5]([O:32][CH2:33][CH3:34])[C:4]([OH:35])=[O:3])=[CH:8][CH:9]=3)[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][S:20][C:19]=2[CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 98918443-(4-[2-(6,11-Dihydrodibenzo[b,e]thiepin-11-yloxy)-ethoxy]-phenyl)-2-ethoxy-propionic acid ethyl ester

Product 1

HCID 99341713-(4-[2-(6,11-Dihydrodibenzo[b,e]thiepin-11-yloxy)-ethoxy]-phenyl)-2-ethoxy-propionic acidYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(4-[2-(6,11-Dihydrodibenzo[b,e]thiepin-11-yloxy)-ethoxy]-phenyl)-2-ethoxy-propionic acid ethyl ester (example 2) (220 mg, 0.44 mmol) in ethanol (5 mL) was added NaOH 1N (0.9 mL, 0.9 mmol). The mixture was stirred at room temperature for 16 h. The ethanol was evaporated of and pH adjusted with HCl 1N to pH 1. After extraction with dichloromethane the product was purified by chromatography, using dichloromethane/methanol (9:1) as eluent, to give 126 mg (62%) of the title compound: 1H NMR (300 MHz, CDCl3) δ1.15 (t, 3H), 2.85-3.10 (m, 2H), 3.32-3.42 (m,1 H), 3.52-3.65 (m,1 H), 2.85 (t, 2H), 3.95-4.05 (m, 1H), 4.10-4.22 (m, 2H), 4.5-5.1 (bs, 1H), 5.60-5.75 (bs, 1H), 6.82 (d, 2H), 7.05-7.50 (m, 10H).

Workup

  1. customThe ethanol was evaporated of and
  2. extractionAfter extraction with dichloromethane the product
  3. customwas purified by chromatography

Sources & evidence

ORD record
ord-dce4288f46304370b82e85c476dccf3c
Source dataset
uspto-grants-2003_02
Patent number
US06525086B2

Reaction notes

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