Sodium Bicarbonate → HCID 9829001, compound

HRID 1107932Notes

Reaction equation

HRID 1107932 reaction equation
[OH:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][C:5]([C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:15])=[CH:4][C:3]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl[S:29]([C:32]1[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[C:34]([OH:41])[CH:33]=1)(=[O:31])=[O:30].C([O-])(O)=O.[Na+]>C1COCC1>[C:14]([C:5]1[CH:4]=[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:2]([O:1][S:29]([C:32]2[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[C:34]([OH:41])[CH:33]=2)(=[O:31])=[O:30])=[C:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=1)(=[O:15])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 516892Sodium Bicarbonate3×HCID 146685314-(Chlorosulfonyl)-2-hydroxybenzoic acid3×HCID 18786173HCID 18786173, compound

Product 1

HCID 9829001HCID 9829001, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At ambient temperature, to a stirred solution of (2'-hydroxy-[1,1';3',1"]terphenyl-5'-yl)-phenyl-methanone (2.02 g, 5.77 mmol) in THF (55 mL) was added portionwise 4-chlorosulphonyl-2-hydroxybenzoic acid (2.70 g, 11.4 mmol, RN 98273-15-5) while maintaining the pH at 8 with the simultaneous addition of 0.5M aq. NaHCO3. After the addition was complete the reaction was stirred for 3.5 h. To the reaction was added 4-chlorosulphonyl-2-hydroxybenzoic acid (2.70 g, 11.4 mmol) while maintaining the pH at 8 with the simultaneous addition of 0.5 M aq. NaHCO3. After the addition was complete the reaction was stirred for 18 h. To the reaction was added 4-chlorosulphonyl-2-hydroxybenzoic acid (2.05 g, 8.66 mmol) while maintaining the pH at 8 with the simultaneous addition of 0.5M aq. NaHCO3. After 2h, the reaction was quenched with 2N HCl (25 mL), extracted with EtOAc and concentrated. Purification by preparative HPLC (C18, eluting with 75% CH3CN/H2O containing 0.1% TFA) and crystallization from EtOAc/hexane gave 0.65 g (20%) of the title compound as a yellow solid, mp 217° C.; 1H NMR (DMSO-d6) δ 6.60 (d, 1H), 6.74 (dd, 1H), 7.30-7.35 (m, 6H), 7.46-7.49 (m, 4H), 7.57-7.61 (m, 3H), 7.68-7.72 (m, 3H), 7.83-7.85 (m, 2H). mass spectrum (EI) ml/z 550 (M+). Anal. Calcd. for C32H22O7S 0.4H2O: C,68.91; H,4.12; N,0.00. Found: C,68.87; H,4.10; N,0.16.

Workup

  1. temperaturewhile maintaining the pH at 8
  2. additionAfter the addition
  3. temperaturewhile maintaining the pH at 8
  4. additionAfter the addition
  5. stirringwas stirred for 18 h
  6. temperaturewhile maintaining the pH at 8
  7. customAfter 2h, the reaction was quenched with 2N HCl (25 mL)
  8. extractionextracted with EtOAc
  9. concentrationconcentrated
  10. customPurification
  11. washby preparative HPLC (C18, eluting with 75% CH3CN/H2O containing 0.1% TFA) and crystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-47085b50c3f64bfbb9ee2d040c2582ce
Source dataset
uspto-grants-2000_05
Patent number
US06063815

Reaction notes

Loading…