Sodium Hydroxide → (+/-)-3-[4-(2'-Butoxy-5'-methyl-biphenyl-4-ylmethoxy)-phenyl]-3-(4-fluorophenyl)-propionic acid

HRID 1160313Notes

Reaction equation

HRID 1160313 reaction equation
C([O:3][C:4](=[O:40])[CH2:5][CH:6]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[C:32]([CH3:34])[CH:31]=[CH:30][C:29]=3[O:35][CH2:36][CH2:37][CH2:38][CH3:39])=[CH:24][CH:23]=2)=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C1COCC1>[CH2:36]([O:35][C:29]1[CH:30]=[CH:31][C:32]([CH3:34])=[CH:33][C:28]=1[C:25]1[CH:26]=[CH:27][C:22]([CH2:21][O:20][C:17]2[CH:18]=[CH:19][C:14]([CH:6]([C:7]3[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=3)[CH2:5][C:4]([OH:40])=[O:3])=[CH:15][CH:16]=2)=[CH:23][CH:24]=1)[CH2:37][CH2:38][CH3:39]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 591326263-[4-(2'-Butoxy-5'-methyl-biphenyl-4-ylmethoxy)-phenyl]-3-(4-fluorophenyl)-propionic acid ethyl ester

Product 1

HCID 59132649(+/-)-3-[4-(2'-Butoxy-5'-methyl-biphenyl-4-ylmethoxy)-phenyl]-3-(4-fluorophenyl)-propionic acidYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 45.3 (56 mg, 0.1 mmol) and 2N NaOH(aq) solution (0.31 mL, 0.62 mmol) in THF (3 mL) was stirred at room temperature overnight. The reactor mixture was concentrated, treated with dilute HCl, and extracted into ethyl acetate. The organic layer washed with water and concentrated to yield product which was purified by flash chromatography to give compound 45 (40 mg). 1H NMR (500 MHz, CDCl3, ppm), δ 0.9 (t, 3H), 1.4 (m, 2H), 1.65 (m, 2H), 2.35 (s, 3H), 3.05 (m, 2H), 3.9 (t, 2H), 4.5 (t, 1H), 5.05 (s, 2H), 6.8-7.5 (m, 15H). MS ESI (neg.) m/e: 511.0 (M−H).

Workup

  1. concentrationThe reactor mixture was concentrated
  2. additiontreated with dilute HCl
  3. extractionextracted into ethyl acetate
  4. washThe organic layer washed with water
  5. concentrationconcentrated
  6. customto yield product which
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-7c1255a49090417183ddff341d5563e3
Source dataset
uspto-grants-2010_10
Patent number
US07816367B2

Reaction notes

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