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

HRID 1905658

Reaktionsgleichung

Reaktionsgleichung von HRID 1905658
[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 6.5 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), 3.79-3.92 (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-0b9e9f1c740d43d68b4bd709787a1d2c
Quelldatensatz
uspto-grants-1987_03
Patentnummer
US04647558

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