Hexane → HCID 19348514, compound

HRID 1637442Notes

Reaction equation

HRID 1637442 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][OH:12])=[CH:7][C:6]=1[NH:13][C:14](=[O:32])[CH2:15][CH:16]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=1[O:30][CH3:31])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])([CH3:4])([CH3:3])[CH3:2].ClS([N:37]=[C:38]=[O:39])(=O)=O.C(OCC)(=O)C.CCCCCC>O1CCCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][C:38](=[O:39])[NH2:37])=[CH:7][C:6]=1[NH:13][C:14](=[O:32])[CH2:15][CH:16]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=1[O:30][CH3:31])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 70918Chlorosulfonyl isocyanateHCID 19348428HCID 19348428, compound

Product 1

HCID 19348514HCID 19348514, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 401 mg (0.91 mmol) of N-[2-t-butyl-5-(hydroxymethyl)phenyl]-3-(2,4-dimethoxyphenyl)octanamide (prepared as described in Preparation 9) in 4 ml of tetrahydrofuran was cooled to -40° C. in a dry ice-acetonitrile bath. 102 μl (1.17 mmol) of chlorosulfonyl isocyanate were added to the cooled solution, and the resulting mixture was stirred for 2.5 hours. At the end of this time, the reaction was quenched by the addition of a phosphate buffer solution (pH 6.9), and the mixture was then extracted with ethyl acetate. The extract was washed with water and then with a saturated aqueous solution of sodium chloride, after which it was dried. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 30 g of silica gel, using a gradient elution method, with mixtures ethyl acetate of and hexane ranging from 2:1 to 3:1 by volume as the eluent, to give 260 mg (yield 59%) of the title compound as a foam-like substance.

Workup

  1. customAt the end of this time, the reaction was quenched by the addition of a phosphate buffer solution (pH 6.9)
  2. extractionthe mixture was then extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialwith a saturated aqueous solution of sodium chloride, after which it was dried
  5. customThe solvent was removed by distillation under reduced pressure
  6. customthe resulting residue was purified by column chromatography through 30 g of silica gel
  7. washa gradient elution method

Sources & evidence

ORD record
ord-fac797a0502b471983d6834468452a07
Source dataset
uspto-grants-2000_03
Patent number
US06040339

Reaction notes

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