Water → HCID 14674662, compound

HRID 1656307Notes

Reaction equation

HRID 1656307 reaction equation
[C:1]1([CH2:7][CH2:8][NH:9][C:10]([CH2:12][CH2:13][C:14]([N:16]2[CH2:22][CH2:21][CH2:20][C@H:17]2[CH2:18][OH:19])=[O:15])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.O>CS(C)=O>[C:1]1([CH2:7][CH2:8][NH:9][C:10]([CH2:12][CH2:13][C:14]([N:16]2[CH2:22][CH2:21][CH2:20][C@H:17]2[CH:18]=[O:19])=[O:15])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 14674660N-[3-[N-(2-phenylethyl)carbamoyl]propanoyl]-L-prolinol

Product 1

HCID 14674662HCID 14674662, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

N-[3-[N-(2-phenylethyl)carbamoyl]propanoyl]-L-prolinol (490 mg; prepared in reference example 1) was dissolved in dry DMSO (5 ml). Triethylamine (0.79 ml) was added to the solution. A solution of sulfur trioxide-pyridine complex (450 mg) in DMSO (2 ml) was dropped to the solution. After 10 mins' stirring, the solution was 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 and a saturated brine, successively, dried and then evaporated. The residue was purified by column chromatography on silica gel to give the title compound (371 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. dry with materiala saturated aqueous solution of sodium hydrocarbonate and a saturated brine, successively, dried
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-aecb6f8ef2b94347a35d60c9e864604a
Source dataset
uspto-grants-1993_10
Patent number
US05254550

Reaction notes

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