4-Toluenesulfonyl chloride → HCID 22323693, compound

HRID 411857Notes

Reaction equation

HRID 411857 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-448789081b5242249ed20181e1329b4b
Source dataset
uspto-grants-2003_05
Patent number
US06559303B1

Reaction notes

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