Triethylamine → HCID 54437313, compound

HRID 1755781Notes

Reaction equation

HRID 1755781 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C@@H:10]([S:25][CH2:26][C:27]1([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH2:29][CH2:28]1)[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18]C2CCCCO2)[CH:12]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(N(CC)CC)C>CO>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C@@H:10]([S:25][CH2:26][C:27]1([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH2:28][CH2:29]1)[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][OH:18])[CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 54196997HCID 54196997, compound

Product 1

HCID 54437313HCID 54437313, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the tetrahydropyranyl ether of Step 6 (1.552 g, 2.83 mmol) and pyridinium p-toluenesulfonate (176 mg, 0.25 equiv.) in 15 mL of MeOH was stirred at room temperature for 2 days. Triethylamine (100 μL, 1 equiv.) was then added, the solvent evaporated, and the residue purified by flash chromotography on silica with EtOAc:toluene 20:80. Yield 1.189 g, 91%.

Workup

  1. customthe solvent evaporated
  2. customthe residue purified by flash chromotography on silica with EtOAc:toluene 20:80

Sources & evidence

ORD record
ord-1e0a8c8b9d54472bb2d96fecc08d3190
Source dataset
uspto-grants-1995_08
Patent number
US05438141

Reaction notes

Loading…