Hydrochloric Acid → HCID 9857135, compound

HRID 722792Notes

Reaction equation

HRID 722792 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 rt. After 24 h, 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 h. 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). Anal. Calcd. for C15H12O4S.0.5AcOH: 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-bd8f0e24cc434daaab1cec2e8cbf1fa5
Source dataset
uspto-grants-2006_11
Patent number
US07138543B2

Reaction notes

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