4-Toluenesulfonyl chloride → HCID 54091745, compound

HRID 976338Notes

Reaction equation

HRID 976338 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[O:21][CH2:20][CH2:19][N:18]([CH2:22][C:23]3[N:27]=[CH:26][N:25]([CH2:28][CH2:29][OH:30])[N:24]=3)[C@H:17]2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[S:39](Cl)([C:42]1[CH:48]=[CH:47][C:45]([CH3:46])=[CH:44][CH:43]=1)(=[O:41])=[O:40].C(N(CC)CC)C>ClCCl>[F:12][C:9]([F:11])([F:10])[C:7]1[CH:6]=[C:5]([C@H:13]([O:15][C@H:16]2[O:21][CH2:20][CH2:19][N:18]([CH2:22][C:23]3[N:27]=[CH:26][N:25]([CH2:28][CH2:29][O:30][S:39]([C:42]4[CH:48]=[CH:47][C:45]([CH3:46])=[CH:44][CH:43]=4)(=[O:41])=[O:40])[N:24]=3)[C@H:17]2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH3:14])[CH:4]=[C:3]([C:2]([F:1])([F:37])[F:38])[CH:8]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 54532469HCID 54532469, compound

Product 1

HCID 54091745HCID 54091745, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The alcohol from step (a), above, (1.81 g, 3.22 mM) was dissolved in dichloromethane (20 ml), tosyl chloride (1.84 g, 9.66 mM) and triethylamine (1.34 ml, 9.66 mM) were added and the reaction stirred at room temperature for 18 hrs. The solvent was removed and the residue redissolved in ethyl acetate and washed with water and brine, dried (MgSO4) and evaporated. The product was purified on silica eluting with methanol-clichloromethane mixtures (1.87 g).

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue redissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe product was purified on silica eluting with methanol-clichloromethane mixtures (1.87 g)

Sources & evidence

ORD record
ord-9f49f522405048afaf656c958f37457f
Source dataset
uspto-grants-1997_03
Patent number
US05612337

Reaction notes

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