Sodium Hydroxide → (2S)-3-{4-[3-(Biphenyl-4-yloxy)-propoxy]-3-chloro-phenyl}-2-methoxy-propionic acid

HRID 459155Notes

Reaction equation

HRID 459155 reaction equation
C([O:3][C:4](=[O:33])[CH:5]([O:31][CH3:32])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)=[C:9]([Cl:30])[CH:8]=1)C.[OH-].[Na+]>O>[C:21]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:22]=[CH:23][C:18]([O:17][CH2:16][CH2:15][CH2:14][O:13][C:10]2[CH:11]=[CH:12][C:7]([CH2:6][C@H:5]([O:31][CH3:32])[C:4]([OH:33])=[O:3])=[CH:8][C:9]=2[Cl:30])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 694217833-{4-[3-(Biphenyl-4-yloxy)-propoxy]-3-chloro-phenyl}-2-methoxy-propionic acid ethyl ester

Product 1

HCID 69424921(2S)-3-{4-[3-(Biphenyl-4-yloxy)-propoxy]-3-chloro-phenyl}-2-methoxy-propionic acidYield 38%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared as follows: 3-{4-[3-(Biphenyl-4-yloxy)-propoxy]-3-chloro-phenyl}-2-methoxy-propionic acid ethyl ester (0.017 g, 0.037 mmol) was dissolved in 0.25 M ethanolic NaOH solution (0.3 mL, 0.075 mmol). The mixture was stirred 16 hours at room temperature and water was added. The aqueous layer was extracted with Et2O (3×5 mL). The aqueous layer was acidified to pH=1 with 1 N HCl and extracted with Et2O (5×10 mL). The organic layer was dried (MgSO4) and concentrated under vacuum to give the title compound as a yellow oil (0.006 mg, 38%). 1H-NMR (200.15 MHz, CDCl3): δ 7.57–7.25 (m, 9H), 7.0–6.86 (m, 3H), 4.23 (q, 4H, J=6.18), 3.96 (dd, 1H, J=7.24, 4.28), 3.40 (s, 3H), 3.06 (dd, 1H, J=14.5, 4.28), 2.92 (dd, 1H, J=14.5, 7.24), 2.32 (qn, 2H, J=5.92).

Workup

  1. customThe title compound was prepared
  2. extractionThe aqueous layer was extracted with Et2O (3×5 mL)
  3. extractionextracted with Et2O (5×10 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-00a47f327af14bf18dbcc7e6add65c83
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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