4-Toluenesulfonyl chloride → HCID 22323693, compound

HRID 2269682Notes

Reaction equation

HRID 2269682 reaction equation
O[CH2:2][CH2:3][N:4]([S:9][C:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][CH2:6][CH2:7][OH:8].[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>N1C=CC=CC=1.C(Cl)Cl>[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35]([CH2:2][CH2:3][N:4]([S:9][C:10]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:5][CH2:6][CH2:7][O:8][S:35]([C:32]2[CH:33]=[CH:34][C:29]([CH3:39])=[CH:30][CH:31]=2)(=[O:37])=[O:36])(=[O:37])=[O:36])=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 22323650HCID 22323650, compound

Product 1

HCID 22323693HCID 22323693, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

N-(2-hydroxyethyl)-N-tritylsulfenyl-3-amino-1-propanol (5.0 g, 12.64 mmol) is dissolved in pyridine (100 mL) and cooled to 0° C. p-Toluensufonylchloride (2.65 g, 13.9 mmol) is dissolve in CH2Cl2 (50 mL) and added to the reaction mixture at 0° C. via dropping funnel. The reaction is monitored by TLC to completion. The reaction mixture is concentrated in vacuo and the resultant residue is dissolved in EtOAc and washed with H2O (3×50 mL) and brine (2×50 mL). The EtOAc is dried (MgSO4), filtered and concentrated in vacuo. The residue is purified by silica gel column chromatography using EtOAc/hexanes as eluent. The appropriate fractions are pooled and concentrated in vacuo to give the title compound.

Workup

  1. additionadded to the reaction mixture at 0° C.
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. dissolutionthe resultant residue is dissolved in EtOAc
  4. washwashed with H2O (3×50 mL) and brine (2×50 mL)
  5. dry with materialThe EtOAc is dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel column chromatography
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad2f8313b610461e9a599d1319b83aad
Source dataset
uspto-grants-2001_12
Patent number
US06329523B1

Reaction notes

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