Hydrochloric Acid → HCID 11193049, compound

HRID 1782634Notes

Reaction equation

HRID 1782634 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:49])[CH:6]([NH:35][C:36](=[O:48])[C:37]1[CH:42]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:40]=[CH:39][C:38]=1[F:47])[CH2:7][S:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([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:18][CH:17]=2)=[CH:12][CH:11]=1.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:19]2[CH:18]=[CH:17][C:16]([C:13]3[CH:14]=[CH:15][C:10]([CH2:9][S:8][CH2:7][CH:6]([NH:35][C:36](=[O:48])[C:37]4[CH:42]=[C:41]([C:43]([F:46])([F:44])[F:45])[CH:40]=[CH:39][C:38]=4[F:47])[C:5]([OH:49])=[O:4])=[CH:11][CH:12]=3)=[CH:21][CH:20]=2)=[CH:23][CH:24]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59696201HCID 59696201, compound

Product 1

HCID 11193049HCID 11193049, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2 N Sodium hydroxide solution (0.25 mL, 0.5 mmol) was added dropwise to a stirred solution of methyl-3-(4′-dibenzofuran-4-yl-biphen-4ylmethylsulfanyl)-2(2-fluoro-5-trifluoromethylbenzoylamino)-propionate (110 mg, 0.17 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 2 N hydrochloric acid. The reaction mixture was extracted with ethyl acetate (2×10 mL). The combined extract was washed with water, sat'd aq NaCl, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by flash column chromatography (5-10% methanol in methylene chloride) afforded the title compound has a white solid (98 mg).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (2×10 mL)
  2. extractionThe combined extract
  3. washwas washed with water
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash column chromatography (5-10% methanol in methylene chloride)

Sources & evidence

ORD record
ord-0661e5a39dd14691ab85ae8c07e99e14
Source dataset
uspto-grants-2009_03
Patent number
US07498356B2

Reaction notes

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