Beta-Propiolactone → HCID 18973965, compound

HRID 2395041Notes

Reaction equation

HRID 2395041 reaction equation
[C:1]1(=[O:5])[O:4][CH2:3][CH2:2]1.Cl.[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:1](=[O:5])[CH2:2][CH2:3][OH:4])=[CH:26][CH:25]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 2365Beta-Propiolactone2×HCID 8471TriethylamineHCID 18973995HCID 18973995, compound

Product 1

HCID 18973965HCID 18973965, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Propiolactone (0.23 ml) was added to a mixture of 4-[3-(2-benzyloxyphenyl]propyl]benzeneamine hydrochloride (1.26 g) and triethylamine (0.5 ml) in methylene chloride (10 ml) and the mixture was stirred for 18 hours. A further equivalent of propiolactone (0.23 ml) was added and stirring continued for a further 24 hours. The reaction mixture was concentrated and the residue was subjected to flash chromatography on silica eluted with a stepwise gradient of methanol in methylene chloride. The fractions eluting with 5% methanol in methylene chloride were collected, concentrated and subjected to chromatography again, eluting with ethyl acetate to give, after crystallisation from dichloromethane/hexane (1:20 v/v) 4-[3-(2-benzyloxyphenyl)propyl]-N-(3-hydroxypropionyl]benzene amine m.p. 109°-110°, 0.22 g (15%).

Workup

  1. stirringstirring
  2. waitcontinued for a further 24 hours
  3. concentrationThe reaction mixture was concentrated
  4. washeluted with a stepwise gradient of methanol in methylene chloride
  5. washThe fractions eluting with 5% methanol in methylene chloride
  6. customwere collected
  7. concentrationconcentrated
  8. washeluting with ethyl acetate
  9. customto give
  10. customafter crystallisation from dichloromethane/hexane (1:20 v/v) 4-[3-(2-benzyloxyphenyl)propyl]-N-(3-hydroxypropionyl]benzene amine m.p. 109°-110°, 0.22 g (15%)

Sources & evidence

ORD record
ord-6385c206bc5d4e54b2b757aa70647364
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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