4-t-Butylbenzenesulfonyl chloride → N-[(5-{[(4-tert-butylphenyl)sulfonyl]amino}-1-methyl-3-phenyl-1H-indol-2-yl)carbonyl]-L-phenylalanine
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:23]([O:25]CC)=[O:24])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:13])=[C:5]2[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[C:34]([C:38]1[CH:43]=[CH:42][C:41]([S:44](Cl)(=[O:46])=[O:45])=[CH:40][CH:39]=1)([CH3:37])([CH3:36])[CH3:35]>>[C:34]([C:38]1[CH:43]=[CH:42][C:41]([S:44]([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:23]([OH:25])=[O:24])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:13])=[C:5]3[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)(=[O:46])=[O:45])=[CH:40][CH:39]=1)([CH3:37])([CH3:35])[CH3:36]Participants
Procedure
The title compound was prepared from ethyl N-[(5-amino-1-methyl-3-phenyl-1H-indol-2-yl)carbonyl]-L-phenylalaninate and 4-tert-butylbenzenesulfonyl chloride followed the procedure of Example 1 Step 3 as an off-white solid: 1H NMR (DMSO-d6) δ 1.24 (s, 9H, 2.85 (dd, J=13.9, 10.9 Hz, 1H, 3.16 (dd, J=13.9, 4.2 Hz, 1H, 3.48 (s, 3H, 4.66 (ddd, J=13.9, 10.9, 4.2 Hz, 1H, 7.05 (dd, J=8.9, 2.0 Hz, 1H, 7.12-7.32 (m, 11H, 7.40 (d, J=8.8 Hz, 1H, 7.53 (d, J=8.9 Hz, 2H, 7.58 (d, J=8.7 Hz, 2H, 8.98 (d, J=8.2 Hz, 1H, 9.83 (s, 1H, 12.89 (br s, 1H; MS (ESI) m/z 610 (MH+); MS (ESI) m/z 608 [M-H]−; HRMS calcd for C35H36N3O5S: 610.2373; found (ESI+): 610.2362; Anal. calcd for C35H35N3O5S.0.7H2O: C, 67.55; H, 5.90; N, 6.75. Found: C, 67.30; H, 5.93; N, 6.80.
Sources & evidence
- ORD record
- ord-be65875b2730478393f31ceeedf9c5cd
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07442805B2
Reaction notes
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