Benzyl chloroformate → 2-[3-(2-{benzyloxycarbonyl-[4-(4-methanesulfonylamino-phenyl)butyl]amino}ethyl)-2-(3,5-dimethyl-phenyl)-1H-indol-5-yl]-2-methylpropionic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:43])[C:5]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=1)=[C:11]2[CH2:25][CH2:26][NH:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])=[CH:34][CH:33]=1)([CH3:7])[CH3:6])[CH3:2].Cl[C:45]([O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:46]>>[CH2:1]([O:3][C:4](=[O:43])[C:5]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]1[CH:18]=[C:19]([CH3:24])[CH:20]=[C:21]([CH3:23])[CH:22]=1)=[C:11]2[CH2:25][CH2:26][N:27]([C:45]([O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:46])[CH2:28][CH2:29][CH2:30][CH2:31][C:32]1[CH:33]=[CH:34][C:35]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])=[CH:36][CH:37]=1)([CH3:7])[CH3:6])[CH3:2]Participants
3
Reactant 2
Product 1
Procedure
The reaction of 2-(2-(3,5-dimethylphenyl)-3-{2-[4-(4-methanesulfonylaminophenyl)butylamino]ethyl}-1H-indol-5-yl)-2-methylpropionic acid ethyl ester with benzyl chloroformate was carried out according to the procedure of Example 4, Step C, to give the titled compound in 72% yield as a stiff foam; homogeneous by TLC in 95:5 CH2Cl2-MeOH. 500 MHz 1H NMR was complex, owing to the existence of rotamers, but was consistent with the assigned structure. Mass spectrum (ESI): m/e=738 (M+H).
Sources & evidence
- ORD record
- ord-bd336126c6b04c9f837a8c5ff250aa87
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06197975B1
Reaction notes
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