Hydrochloric Acid → HCID 9857135, compound

HRID 1352834Notes

Reaction equation

HRID 1352834 reaction equation
C([S:4][CH2:5][C:6]1[CH:7]=[C:8]([C:22]([O:24]C)=[O:23])[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([O:20]C)=[O:19])[CH:13]=2)=[CH:10][CH:11]=1)(=O)C.[OH-].[Na+].Cl>C1COCC1.O>[SH:4][CH2:5][C:6]1[CH:7]=[C:8]([C:22]([OH:24])=[O:23])[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([OH:20])=[O:19])[CH:13]=2)=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 20728731HCID 20728731, compound

Product 1

HCID 9857135HCID 9857135, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-acetylthiomethyl-[1,1′-biphenyl]-2,3′-dicarboxylic acid, dimethyl ester (0.27 g, 0.75 mmol) in deoxygenated THF was added a degassed solution of sodium hydroxide (0.12 g, 3.0 mmol) in H2O (5 mL) at room temperature. After 24 hours, additional solution of sodium hydroxide (0.09 g) in H2O (2 mL) was added to the reaction mixture and the mixture was stirred for 24 hours. The mixture was acidified with 10% HCl and extracted with EtOAc. The extract was dried over MgSO4 and concentrated. The crude material was purified by column chromatography with (9:1 dichloromethane/EtOAc with 1% acetic acid) to afford 4-mercaptomethyl-[1,1′-biphenyl]-2,3′-dicarboxylic acid (0.20 g, 92%) as a white solid: 1H NMR (DMSO-d6) δ 3.10 (t, J=8.03 Hz, 1H), 3.89 (d, J=8.03 Hz, 2H), 7.43 (d, J=7.53 Hz, 1H), 7.58-7.65 (m, 3H), 7.83 (d, J=2.01 Hz, 1H), 7.92 (s, 1H), 7.97-8.00 (m, 1H). Elemental analysis calculated for C15H12O4S.0.5 AcOH: C, 60.37; H, 4.43; O, 25.13; S, 10.07. Found: C, 60.28; H, 4.45; S, 10.15.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe extract was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude material was purified by column chromatography with (9:1 dichloromethane/EtOAc with 1% acetic acid)

Sources & evidence

ORD record
ord-765e8699d3d949438489de777e295a93
Source dataset
uspto-grants-2007_05
Patent number
US07220780B2

Reaction notes

Loading…