4-Toluenesulfonyl chloride → HCID 23109302, compound

HRID 1781996Notes

Reaction equation

HRID 1781996 reaction equation
[CH2:1]([N:5]1[C:9]2([CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[C:8](=[O:15])[N:7]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:6]1=[O:20])[CH2:2][CH2:3][CH3:4].C(N(CC)C(C)C)(C)C.[O-]S([Cl:33])=O.S(Cl)(C1C=CC(C)=CC=1)(=O)=O.[C:45]1([CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56]O)[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C(#N)C>[ClH:33].[CH2:1]([N:5]1[C:9]2([CH2:14][CH2:13][N:12]([CH2:56][CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH2:11][CH2:10]2)[C:8](=[O:15])[N:7]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:6]1=[O:20])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 5201106-Phenyl-1-hexanolHCID 5099883HCID 5099883, compoundHCID 11448907HCID 11448907, compound

Product 1

HCID 23109302HCID 23109302, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of the compound prepared in Example 1 (28 mg) and N,N-diisopropylethylamine (155 mg) in acetonitrile (3 mL) were added benzenesulfonylchloride resin (Argonaut, product name PS-TsCl, product number 800276, 1.22 mmol/g, 0.20 mmol) (164 mg) and sulfonyl resin (175 mg) which is prepared from 6-phenylhexanol (345 mg). The mixture was stirred for 18 hours at 70° C. and then filtrated. The resin was washed with acetonitrile (3 mL, three times). The filtrate and rinsed solution were combined and concentrated. The residue was purified by column chromatography on silica gel (chloroform:methanol=25:1), added 4N hydrochloric acid in ethyl acetate and concentrated to give the title compound (28 mg) having the following physical data.

Workup

  1. filtrationfiltrated
  2. washThe resin was washed with acetonitrile (3 mL, three times)
  3. washThe filtrate and rinsed solution
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=25:1)
  6. additionadded 4N hydrochloric acid in ethyl acetate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b14c93ecec2d476e8a8652d824d39716
Source dataset
uspto-grants-2009_03
Patent number
US07498323B2

Reaction notes

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