Peracetic Acid → 3[2-(4-Ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-phenylacetamido]-4-methyl-3-methylsulphinylazetidin-2-one

HRID 246866

Reaktionsgleichung

Reaktionsgleichung von HRID 246866
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]([NH:11][CH:12]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:13]([NH:15][C:16]2([S:22][CH3:23])[CH:19]([CH3:20])[NH:18][C:17]2=[O:21])=[O:14])=[O:10])[C:5](=[O:30])[C:4]1=[O:31])[CH3:2].C(OO)(=[O:34])C>O1CCOCC1.C(O)(=O)C>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]([NH:11][CH:12]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:13]([NH:15][C:16]2([S:22]([CH3:23])=[O:34])[CH:19]([CH3:20])[NH:18][C:17]2=[O:21])=[O:14])=[O:10])[C:5](=[O:30])[C:4]1=[O:31])[CH3:2]

Komponenten

5

Edukt 2

HCID 6585Peracetic AcidHCID 201628663[2-(4-Ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-phenylacetamido]-4-methyl-3-methylthioazetidin-2-one

Produkt 1

HCID 201628533[2-(4-Ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-phenylacetamido]-4-methyl-3-methylsulphinylazetidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

The azetidinone (60) (250 mg) in dry dioxan (10 ml) was treated with a (5.07% w/v) solution of peracetic acid in acetic acid (0.69 ml) for 1.5 hour. The solvent was then evaporated in vacuo, the complete removal of acidic residues being ensured. Silica gel chromatography of the residue gave the title compound as a pale--white solid (149 mg), νmax. (Nujol) 3300, 1760, 1710, and 1670 cm-1, δ[(CD3)2SO]0.65, 0.93, 1.16 and 1.19 (each d, J 6.4 Hz, together 3H), (1.07 (t, J 7 Hz, 3H), 1.99, 2.14, 2.39, 2.64 and 2.68 (each s, together 3H), 3.37 (q, J 7 Hz, 2H), 3.47-3.52 (m, 2H), 3.179-3.92 (m, 2H), 3.92-4.10 (complex m, together 1H), [5.45-5.60 (complex m) and 5.86 (d, J 7 Hz), together 1H], 7.27-7.55 (m, 5H), 8.63 and 8.74 br (each s, together 1H, exch), 9.14 and 9.35 br (each s, together 1H, exch.) and 9.65-10.00 (complex m, together 1H, exch).

Aufarbeitung

  1. customThe solvent was then evaporated in vacuo
  2. customthe complete removal of acidic residues being

Quellen und Nachweise

ORD-Eintrag
ord-705f4981fefa4c3ba716638b5401e372
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04704385

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