2-Mesitylenesulfonyl chloride → HCID 14677687, compound

HRID 2073555Notes

Reaction equation

HRID 2073555 reaction equation
[OH:1][CH:2]([CH:5]1[O:9][C:8]2[CH:10]=[CH:11][C:12]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:7]=2[CH2:6]1)[CH2:3][OH:4].[CH3:19][C:20]1[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[C:21]=1[S:28](Cl)(=[O:30])=[O:29]>N1C=CC=CC=1>[OH:1][CH:2]([CH:5]1[O:9][C:8]2[CH:10]=[CH:11][C:12]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:7]=2[CH2:6]1)[CH2:3][O:4][S:28]([C:21]1[C:22]([CH3:27])=[CH:23][C:24]([CH3:26])=[CH:25][C:20]=1[CH3:19])(=[O:30])=[O:29]

Participants

4

Reactant 2

HCID 130462-Mesitylenesulfonyl chloride2×HCID 14677686HCID 14677686, compound

Product 1

HCID 14677687HCID 14677687, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The compound of Example 7, (430 mg, 1.7 mmoles) was taken up in dry pyridine (20 ml) and cooled to 0° under N2. 2,4,6-Trimethylphenylsulfonyl chloride (400 mg) was added at 0° and stirring was continued overnight at 0°. Additional 2,4,6-trimethylphenylsulfonyl chloride (75 mg) was added, and stirring was continued at 5° for 24 hours. The pyridine was removed under high vacuum and the residue was taken up in CHCl3, washed with dilute HCl, brine, dried and concentrated. Chromatography of the residue on silica gel using ethyl acetate gave the title compound as a mixture of the two diastereoisomers. NMR (90 MHz) (CDCl3) (ppm) 2.37 (3H, s), 2.67 (6H, s), 2.5-2.8 (1H, br), 3.27 (2H, d), 3.57 (2H, s), 3.70 (3H, s), 3.9-4.3 (3H, m), 4.75 (1H, m), 6.73 (1H, d), 6.97-7.25 (4H, m).

Workup

  1. temperaturecooled to 0° under N2
  2. stirringstirring
  3. waitwas continued at 5° for 24 hours
  4. customThe pyridine was removed under high vacuum
  5. washwashed with dilute HCl, brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-78a800fca5fa41e989fb038a90f3621e
Source dataset
uspto-grants-1990_04
Patent number
US04918092

Reaction notes

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