Hydrochloric Acid → HCID 66896793, compound

HRID 1394633Notes

Reaction equation

HRID 1394633 reaction equation
C[O:2][C:3](=[O:32])[CH:4]=[C:5]([C:7]1[CH:31]=[CH:30][C:10]2[S:11][CH:12]=[C:13]([C:14]3[CH:19]=[C:18]([CH:20]([CH3:22])[CH3:21])[CH:17]=[C:16]([CH:23]([CH3:25])[CH3:24])[C:15]=3[O:26]COC)[C:9]=2[CH:8]=1)[CH3:6].Cl>CO.[OH-].[Na+]>[OH:26][C:15]1[C:16]([CH:23]([CH3:24])[CH3:25])=[CH:17][C:18]([CH:20]([CH3:22])[CH3:21])=[CH:19][C:14]=1[C:13]1[C:9]2[CH:8]=[C:7]([C:5]([CH3:6])=[CH:4][C:3]([OH:32])=[O:2])[CH:31]=[CH:30][C:10]=2[S:11][CH:12]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69217498HCID 69217498, compound

Product 1

HCID 66896793HCID 66896793, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

3-[3-(3,5-Di-iso-propyl-2-methoxymethoxyphenyl)-benzo[b]thien-5-yl]-but-2-enoic acid methyl ester (15 mg, 0.033 mmol) (see Example 55, step F) was dissolved in MeOH (2 ml) and 1N NaOH (2 ml). The mixture was then stirred at 60° C. for 2 h, then cooled to ambient temperature and brought to pH 2 with 1N HCl . The reaction mixture was allowed to stir for 1 h, it was extracted with ethyl acetate (3×5 mL) and the organic layers were dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel chromatography (10% ethyl acetate in hexanes) to give 3-[3-(2-hydroxy-3,5-diisopropyl-phenyl)-benzo[b]thien-5-yl]-but-2-enoic acid as a white solid (11.7 mg, 89%). 1H NMR (250 MHz, CDCl3): δ 7.89 (d, 1H, J=8.75), 7.70 (d, 1H, J=0.62), 7.50 (m, 2H), 7.08 (d, 1H, J=1.2), 6.95 (d, 1H, J=1.2), 6.14 (bs, 1H), 3.29 (m, 1H), 2.85 (m, 1H), 2.55 (s, 3H), 1.27 (s, 3H), 1.25 (s, 3H), 1.23 (s, 3H), 1.20 (s, 3H). MS [EI+] 395 (M+H−H2O)+, [EI−] 393 (M−1)−. HPLC [MetaSil AQ C18 (0.46×25 cm) 95% CH3CN(0.1% TFA) in H2O(0.1% TFA)] 4.388 min.

Workup

  1. temperaturecooled to ambient temperature
  2. stirringto stir for 1 h
  3. extractionit was extracted with ethyl acetate (3×5 mL)
  4. dry with materialthe organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-807d0550a7744ec085be9bc77d4c5a1f
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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