Hydrochloric Acid → HCID 11669320, compound

HRID 2375978Notes

Reaction equation

HRID 2375978 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:35])[CH:6]([S:8][CH2:9][C:10]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[C:27]4[O:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=5[C:26]=4[CH:25]=[CH:24][CH:23]=3)[CH:17]=2)[CH:13]=[CH:12][CH:11]=1)[CH3:7].Cl>O1CCCC1.CO.O>[CH:25]1[C:26]2[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[O:28][C:27]=2[C:22]([C:18]2[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=2)[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:9][S:8][CH:6]([CH3:7])[C:5]([OH:35])=[O:4])[CH:15]=2)=[CH:23][CH:24]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131727231HCID 131727231, compound

Product 1

HCID 11669320HCID 11669320, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2N Sodium hydroxide solution (0.33 mL, 0.66 mmol) was added dropwise to a stirred solution of methyl-2-(3′-dibenzofuran-4-yl-biphen-3-ylmethylsulfanyl)-propionate (100 mg, 0.22 mmol) in tetrahydrofuran (5 mL) and methanol (1 mL). The clear reaction mixture was stirred at room temperature until the reaction was complete (TLC control), and then diluted with water (5 mL), and acidified to pH 3 with 2N hydrochloric acid. The reaction mixture was extracted with ethyl acetate (2×20 mL). The combined extract was washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification of the product by flash column chromatography, using 5-10% methanol in methylene chloride as eluent, afforded the title compound has a white solid (86 mg, 89%); Rf: 0.40 (10% methanol in dichloromethane); 1H NMR (DMSO-d6): □ 8.19 (2H, m, Ar—H), 8.02 (2H, d, J=9 Hz, Ar—H), 7.86 (2H, d, J=9 Hz, Ar—H), 7.75 (4H, m, Ar—H), 7.29-7.41 (5H, m, Ar—H), 3.96 (2H, s, PhCH2S), 3.36 (1H, q, J=7 Hz, SCHMe), 1.36 (3H, d, J=7 Hz, CHMe); ESI-LCMS e/z calcd for C28H22O3S 438.54, found 439 (M+H)+.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (2×20 mL)
  2. extractionThe combined extract
  3. washwas washed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the product by flash column chromatography

Sources & evidence

ORD record
ord-d81ffe803596479e906d6e6977fa40df
Source dataset
uspto-grants-2008_12
Patent number
US07465825B2

Reaction notes

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