Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 10206342, compound

HRID 844341Notes

Reaction equation

HRID 844341 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]([CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][C@H:13]1[C@@H:17]([O:18]C2CCCCO2)[CH2:16][C@@H:15]([O:25]C2CCCCO2)[C@@H:14]1[CH2:32][O:33][C:34](=[S:44])[NH:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[CH:38]=1)=[O:6].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[OH:18][C@H:17]1[CH2:16][C@@H:15]([OH:25])[C@H:14]([CH2:32][O:33][C:34](=[S:44])[NH:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[CH:38]=2)[C@H:13]1[CH2:12]/[CH:11]=[CH:10]\[CH2:9][CH2:8][CH2:7][C:5](=[O:6])[NH:4][CH2:3][CH2:2][OH:1]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86758009HCID 86758009, compound

Product 1

HCID 10206342HCID 10206342, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of bis-THP ether 8a (40 mg, 0.062 mmol) and pyridinium p-toluenesulfonate (5 mg) in MeOH (1.5 mL) was stirred at 23° C. for 16 h. The solvent was removed in vacuo and the residue was diluted with EtOAc and washed with 1N HCl, saturated aqueous NaHCO3 and brine. The organic portion was dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 100% EtOAc followed by 9:1 EtOAc/MeOH) provided 20 mg of the above titled compound.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with EtOAc
  3. washwashed with 1N HCl, saturated aqueous NaHCO3 and brine
  4. dry with materialThe organic portion was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash column chromatography (silica gel, 100% EtOAc followed by 9:1 EtOAc/MeOH)

Sources & evidence

ORD record
ord-0a998b865827491fb0ffeee09916d78e
Source dataset
uspto-grants-2002_04
Patent number
US06380250B1

Reaction notes

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