Beta-Propiolactone → HCID 57860738, compound

HRID 1513596Notes

Reaction equation

HRID 1513596 reaction equation
[CH3:1][O:2][C:3]1[C:7]2[C:8](=[O:25])[N:9]([CH2:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]=2[N:5]([CH3:26])[C:4]=1[C:27]([NH:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=[O:28].C(N(CC)CC)C.C1COCC1.[C:48]1(=[O:52])[O:51][CH2:50][CH2:49]1>C(OCC)(=O)C>[OH:52][CH2:48][CH2:49][C:50]([N:33]1[CH2:32][CH2:31][CH:30]([NH:29][C:27]([C:4]2[N:5]([CH3:26])[C:6]3[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[N:9]([CH2:16][C:17](=[O:24])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:8](=[O:25])[C:7]=3[C:3]=2[O:2][CH3:1])=[O:28])[CH2:35][CH2:34]1)=[O:51]

Participants

6

Reactant 4

HCID 2365Beta-PropiolactoneHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 57860479HCID 57860479, compound

Product 1

HCID 57860738HCID 57860738, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of the compound of Example 77 (200 mg, 0.423 mmol), triethylamine (423 μL, 3.18 mmol) and THF (10 mL) was added β-propiolactone (39.9 μL, 0.635 mmol) at 0° C., and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by aminosilica gel chromatography (eluate; ethyl acetate). Recrystallization of the obtained solid from ethyl acetate gave the title compound (70.0 mg, 30%) as a white powder.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by aminosilica gel chromatography (eluate; ethyl acetate)
  5. customRecrystallization of the obtained solid from ethyl acetate

Sources & evidence

ORD record
ord-895a7650fd1d4dae871a65ed53b85cd2
Source dataset
uspto-grants-2012_07
Patent number
US08217176B2

Reaction notes

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