Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 86762397, compound

HRID 1023414Notes

Reaction equation

HRID 1023414 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[C:10]([CH2:12][O:13]C2CCCCO2)[CH:9]=[CH:8][C:7]=1[C:20]1[N:24]=[C:23]([CH2:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:22][N:21]=1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CO>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][C:7]=1[C:20]1[N:24]=[C:23]([CH2:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[O:22][N:21]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86762398HCID 86762398, compound

Product 1

HCID 86762397HCID 86762397, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of Intermediate 9 (1.02 g, 2.2 mmol) in methanol (20 mL) was added PPTS (56 mg). After heating to 55° C. for 24 h, the reaction mixture was cooled to RT and concentrated. Purification by MPLC (30% ethyl acetate in hexanes) gave 621 mg of Intermediate 16 as a colorless oil.

Workup

  1. temperaturethe reaction mixture was cooled to RT
  2. concentrationconcentrated
  3. customPurification by MPLC (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d7f707e65cbf404d8301b4ef88fd3f8f
Source dataset
uspto-grants-2014_05
Patent number
US08722712B2

Reaction notes

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