4-Cyanobenzoyl isocyanate → t-butyl (2S)-2-(n-butylsulphonylamino)-3-[4-[3-(4-cyanobenzoyl)ureido]phenyl]propionate
Reaction equation
[CH2:1]([S:5]([NH:8][C@@H:9]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=1)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].[C:25]([C:27]1[CH:37]=[CH:36][C:30]([C:31]([N:33]=[C:34]=[O:35])=[O:32])=[CH:29][CH:28]=1)#[N:26]>C(#N)C>[CH2:1]([S:5]([NH:8][C@@H:9]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([NH:24][C:34]([NH:33][C:31](=[O:32])[C:30]2[CH:36]=[CH:37][C:27]([C:25]#[N:26])=[CH:28][CH:29]=2)=[O:35])=[CH:22][CH:23]=1)[C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])(=[O:6])=[O:7])[CH2:2][CH2:3][CH3:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In a similar manner to Example 1, starting material step (c), the product of step (c) (2.59 g) and 4-cyanobenzoyl isocyanate (1.29 g) in acetonitrile (100 ml total) were reacted to give, after stirring at ambient temperature for 1 hour and storage at 10° C. overnight, a solid, which was crystallised from isopropanol to give t-butyl (2S)-2-(n-butylsulphonylamino)-3-[4-[3-(4-cyanobenzoyl)ureido]phenyl]propionate (2.32 g) as a white solid: m.p. 171°-173° C.; NMR Spectrum (CDCl3) 0.90 (3H, t), 1.37 (2H, m), 1.49 (9H, s), 1.73 (2H, m), 2.90 (2H, t), 3.11 (2H, m), 4.31 (1H, m), 5.61 (1H, d), 7.19 (2H, d), 7.42 (2H, d), 7.83 (2H, d), 8.19 (2H, d), 9.92 (1H, br s), 10.78 (1H, br s); Mass Spectrum m/Z 529 (M+H)+.
Workup
- customto give
- customstorage at 10° C. overnight, a solid, which was crystallised from isopropanol
Sources & evidence
- ORD record
- ord-f372551bc93d4831ab3e78803fe3dce7
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05576334
Reaction notes
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