Water → HCID 15712741, compound

HRID 257442Notes

Reaction equation

HRID 257442 reaction equation
[CH:1]([CH:4]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:5]([N:7]1[CH2:13][CH2:12][CH2:11][C@H:8]1[CH2:9][OH:10])=[O:6])([CH3:3])[CH3:2].C(N(CC)CC)C.O>CS(C)=O>[CH:1]([CH:4]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:5]([N:7]1[CH2:13][CH2:12][CH2:11][C@H:8]1[CH:9]=[O:10])=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 15712734HCID 15712734, compound

Product 1

HCID 15712741HCID 15712741, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

N-(2-isopropyl-6-phenylhexanoyl)-L-prolinol was dissolved in dry DMSO (1.5 ml). Triethylamine (0.35 ml) was added to this solution. A solution of sulfur trioxide-pyridine complex (414 mg) in DMSO (1 ml) was dropped to this solution. The solution was stirred for 10 mins and poured into water. The mixture was extracted with ethyl acetate. The oily layer was washed with 1N hydrochloric acid, a saturated aqueous solution of sodium hydrocarbonate, followed by saturated brine, dried and evaporated. The residue was purified by column chromatography on silica gel to give the title compound (150 mg) having the following physical data:

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe oily layer was washed with 1N hydrochloric acid
  3. customdried
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-91a00f3bf8fe4ebfbce04a56ab47c94d
Source dataset
uspto-grants-1993_11
Patent number
US05262431

Reaction notes

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