Ammonia → 3-Amino-3[2-(4-ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-phenylacetamido]-4-methylazetidin-2-one

HRID 2118559

Reaction equation

HRID 2118559 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]([NH:11][CH:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:13]([NH:15][C:16]2(S(C)=O)[CH:19]([CH3:20])[NH:18][C:17]2=[O:21])=[O:14])=[O:10])[C:5](=[O:31])[C:4]1=[O:32])[CH3:2].[NH3:33]>O1CCOCC1>[NH2:33][C:16]1([NH:15][C:13](=[O:14])[CH:12]([NH:11][C:9]([N:6]2[CH2:7][CH2:8][N:3]([CH2:1][CH3:2])[C:4](=[O:32])[C:5]2=[O:31])=[O:10])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:19]([CH3:20])[NH:18][C:17]1=[O:21]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 201628533[2-(4-Ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-phenylacetamido]-4-methyl-3-methylsulphinylazetidin-2-one

Product 1

HCID 201628613-Amino-3[2-(4-ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-phenylacetamido]-4-methylazetidin-2-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The sulphoxide (61) (145 mg) in dioxan (5 ml) was treated with ammonia (21 ml) overnight at room temperature. The solvent was then evaporated and the residue chromatographed on silica gel to give the product (62) as a white solid (95 mg), νmax. (CHCl3) 3400, 3280, 1770, 1715 and 1690 cm-1, δ(CDCl3) 0.87, 0.90, 1.10 and 1.14 (each d, J6 Hz, together 3H), 1.20 (t, J7 Hz, 3H), 1.6-2.9 br (2H, exch.), 3.40-3.65 (m, 4H) (irradiation at 0.90 caused this signal to simplify), 3.85 (2×q, J7 Hz, together 1H) (irradiation at 0.87 or 1.10 caused one of the above signals to collapse to a s), 3.95-4.13(m, 2H), 5.45(2×d, J7 Hz, together 1H, collapses to 2×s on exch), 6.50, 6.58, 6.63, and 6.72 br (each s, together 1H, exch.), 7.25-7.56 (m, 5H), 7.62, 7.76, 7.90, and 8.06 br (each s, 1H, exch.), and 9.90 (2×d, J7 Hz, together 1H, exch.).

Workup

  1. customThe solvent was then evaporated
  2. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-9601222c819742a4afe196f9468618ed
Source dataset
uspto-grants-1987_07
Patent number
US04678782

Linked notes

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