Triphenylphosphine → HCID 70225626, compound
Reaction equation
[C:1]([O:5][C:6](=[O:49])[N:7]([CH2:27][CH2:28][C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([N:38]=[C:39]=[O:40])[CH:36]=2)[NH:31][C:30]=1[C:41]1[CH:46]=[C:45]([CH3:47])[CH:44]=[C:43]([CH3:48])[CH:42]=1)[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([S:19]([CH3:22])(=[O:21])=[O:20])[C:13]=1[S:23]([CH3:26])(=[O:25])=[O:24])([CH3:4])([CH3:3])[CH3:2].[N:50]([CH2:53][C:54]([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)=O)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[C:1]([O:5][C:6](=[O:49])[N:7]([CH2:27][CH2:28][C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([NH:38][C:39]3[O:40][C:54]([C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)=[CH:53][N:50]=3)[CH:36]=2)[NH:31][C:30]=1[C:41]1[CH:42]=[C:43]([CH3:48])[CH:44]=[C:45]([CH3:47])[CH:46]=1)[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([S:19]([CH3:22])(=[O:21])=[O:20])[C:13]=1[S:23]([CH3:26])(=[O:25])=[O:24])([CH3:3])([CH3:2])[CH3:4]Participants
4
Procedure
To a solution of {2-[2-(3,5-dimethylphenyl)-5-isocyanato-1H-indol-3-yl]ethyl}-[4-(4-amino(dimethanesulfonyl)phenyl)butyl] carbamic acid tert-butyl ester (30 mg in 0.50 mL dry methylene chloride) was added 9 mg of 2-azido-1-phenyl-ethanone followed by 14 mg triphenylphosphine and the mixture stirred at room temperature. After 4 hours, the mixture was applied to a silica gel column for purification by flash chromatography (hexane:ethyl acetate, 3:2; then 1:1; then 2:3; then 1:3) to give the title compound (13 mg).
Workup
- customthe mixture was applied to a silica gel column for purification by flash chromatography (hexane
Sources & evidence
- ORD record
- ord-93d1e23311c141e7a057c6578b4ee5eb
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06197975B1
Reaction notes
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