4-t-Butylbenzenesulfonyl chloride → N-[(5-{[(4-tert-butylphenyl)sulfonyl]amino}-1-methyl-3-phenyl-1H-indol-2-yl)carbonyl]-L-leucine
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([C:12]([NH:14][C@H:15]([C:20]([O:22]C)=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])=[O:13])=[C:5]2[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:30]([C:34]1[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1)([CH3:33])([CH3:32])[CH3:31]>>[C:30]([C:34]1[CH:39]=[CH:38][C:37]([S:40]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]([CH3:11])[C:6]([C:12]([NH:14][C@H:15]([C:20]([OH:22])=[O:21])[CH2:16][CH:17]([CH3:18])[CH3:19])=[O:13])=[C:5]3[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)(=[O:42])=[O:41])=[CH:36][CH:35]=1)([CH3:33])([CH3:31])[CH3:32]Participants
Procedure
The title compound was prepared from methyl N-[(5-amino-1-methyl-3-phenyl-1H-indol-2-yl)carbonyl]-L-leucinate and 4-tert-butylbenzenesulfonyl chloride followed the procedure of Example 1 Step 3 as an off-white solid: 1H NMR (DMSO-d6) δ 0.78 (d, J=6.3 Hz, 3H, 0.79 (d, J=6.0 Hz, 3H, 1.24 (s, 9H, 1.30-1.60 (m, 3H, 3.74 (s, 3H, 4.25-4.35 (m, 1H), 7.08 (dd, J=8.8, 2.0 Hz, 1H, 7.25-7.32 (m, 4H, 7.33-7.40 (m, 2H, 7.45 (d, J=7.9 Hz, 1H), 7.54 (d, J=7.8 Hz, 2H, 7.59 (d, J=8.7 Hz, 2H, 8.76 (d, J=7.8 Hz, 1H, 9.85 (s, 1H, 12.64 (br s, 1H; MS (ESI) m/z 576 (MH+); MS (ESI) m/z 574 [M-H]−; HRMS calcd for C32H38N3O5S: 576.2530; found (ESI+): 576.2518; Anal. calcd for C32H37N3O5S.0.5H2O: C, 65.73; H, 6.55; N, 7.19. Found: C, 65.41; H, 6.45; N, 7.16.
Sources & evidence
- ORD record
- ord-6116565c5f8740c2b9435c40de3287c0
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07442805B2
Reaction notes
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