Hydrochloric Acid → HCID 11619028, compound

HRID 2113205Notes

Reaction equation

HRID 2113205 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][CH2:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:25]4[O:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[C:24]=4[CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.[OH-].[K+].Cl>C1COCC1.CO.C(OCC)(=O)C>[CH:23]1[C:24]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[O:26][C:25]=2[C:20]([C:17]2[CH:18]=[CH:19][C:14]([C:11]3[CH:12]=[CH:13][C:8]([CH2:7][S:6][CH2:5][CH2:4][C:3]([OH:33])=[O:2])=[CH:9][CH:10]=3)=[CH:15][CH:16]=2)=[CH:21][CH:22]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 59855502HCID 59855502, compound

Product 1

HCID 11619028HCID 11619028, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(4′-dibenzofuran-4-yl-biphen-4-ylmethylsulfanyl)-propanoic acid methyl ester (210 mg, 0.46 mmol) in THF (2 mL) and methanol (2 mL) was cooled to 0° C. and treated with 2 N KOH (1.0 mL). After stirring at room temperature for 1 h the solution was acidified with 10% HCl to pH 2 and diluted with ethyl acetate (25 mL). After being seperated, the aqueous layer was extracted with ethyl acetate (3×15 mL) and the combined organic layers were dried over MgSO4 and concentrated. Purification by flash column chromatography (2-5% methanol in dichloromethane) provided 3-(4′-dibenzofuran-4-yl-biphen-4-ylmethylsulfanyl)-propanoic acid (180 mg, 90%) as white solid. 1H NMR (CDCl3), 8.01 (d, J=8 Hz, 2H), 7.94 (d, J=8 Hz, 2H), 7.78 (d, J=8 Hz, 2H), 7.66 (m, 4H), 7.42 (m, 5H), 3.82 (s, 2H), 3.82 (s, 2H), 2.76 (m, 2H), 2.56 (t, J=6 Hz, 2H). LCMS 462 (M++23).

Workup

  1. customAfter being seperated
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×15 mL)
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (2-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-168f9e53917947a1bb8737ee529bb197
Source dataset
uspto-grants-2009_04
Patent number
US07524878B2

Reaction notes

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