Triphenylphosphine → [4-(2,5-Dimethyl-phenyl)-piperazin-1-yl]-[1-(toluene-4-sulfonyl)-aziridin-2-yl]-methanone

HRID 1864376Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:30])[CH:16]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH2:17]O)[CH2:11][CH2:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([C:15]([CH:16]2[CH2:17][N:19]2[S:20]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[O:30])[CH2:11][CH2:10]1

Participants

Reactant 3

HCID 11776Triphenylphosphine

HCID 5462977Diethyl azodicarboxylate

HCID 67141132N-{2-[4-(2,5-dimethyl-phenyl)-piperazin-1-yl]-1-hydroxymethyl-2-oxo-ethyl}-4-methyl-benzenesulfonamide

Product 1

HCID 86623481[4-(2,5-Dimethyl-phenyl)-piperazin-1-yl]-[1-(toluene-4-sulfonyl)-aziridin-2-yl]-methanone

Procedure

In analogy to example 2, N-{2-[4-(2,5-dimethyl-phenyl)-piperazin-1-yl]-1-hydroxymethyl-2-oxo-ethyl}-4-methyl-benzenesulfonamide was reacted with triphenylphosphine and diethylazodicarboxylate to give [4-(2,5-dimethyl-phenyl)-piperazin-1-yl]-[1-(toluene-4-sulfonyl)-aziridin-2-yl]-methanone.

Sources & evidence

ORD record: ord-198e02a9273c4e37873c29faffae3bb4
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625902B2

Reaction notes

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