tert-Butyl hydroperoxide → Phenyl-3-(N-carbobenzyloxyleucyl)amino-4-phenylbut-2-enyl Sulfone

HRID 2111541Notes

Reaction equation

HRID 2111541 reaction equation
[C:1]1([CH:7]([C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=2)[C@@H:8]([NH:49][C:50](=[O:67])[C@H:51]([CH2:63][CH:64]([CH3:66])[CH3:65])[NH:52][C:53]([O:55][CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)=[O:54])[CH:9]=[CH:10][S:11]([CH:14]=[CH:15][C@H:16]([NH:30][C:31](=[O:48])[C@H:32]([CH2:44][CH:45]([CH3:47])[CH3:46])[NH:33][C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:35])[CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:13])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.C(OO)(C)(C)C.C1(C(C2C=CC=CC=2)[C@H](NC(=O)[C@H](CC(C)C)NC(OCC2C=CC=CC=2)=O)C=CS(C=C[C@@H](NC(=O)[C@H](CC(C)C)NC(OCC2C=CC=CC=2)=O)C(C2C=CC=CC=2)C2C=CC=CC=2)(=O)=O)C=CC=CC=1>C1COCC1>[C:18]1([CH:17]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:16]([NH:30][C:31](=[O:48])[C@H:32]([CH2:44][CH:45]([CH3:46])[CH3:47])[NH:33][C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:35])=[CH:15][CH2:14][S:11]([CH2:10][CH:9]=[C:8]([NH:49][C:50](=[O:67])[C@H:51]([CH2:63][CH:64]([CH3:66])[CH3:65])[NH:52][C:53]([O:55][CH2:56][C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)=[O:54])[CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:68]2[CH:69]=[CH:70][CH:71]=[CH:72][CH:73]=2)(=[O:12])=[O:13])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 6410tert-Butyl hydroperoxideHCID 86608592HCID 86608592, compoundHCID 86608593Phenyl-(3R)-3-(N-carbobenzyloxyleucyl)amino-4-phenylbut-1-enyl SulfoneHCID 178418339Butyllithium

Product 1

HCID 86608591Phenyl-3-(N-carbobenzyloxyleucyl)amino-4-phenylbut-2-enyl SulfoneYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cbz-Leu-D-Phe-VS-Ph was treated with butyllithium and tert-butylhydroperoxide in freshly distilled THF as described with Cbz-Leu-Phe-VS-Ph above to give Cbz-Leu-Phe-AS-Ph (Isomer B) as a white powder, yield 15%. 1H-NMR (CDCl3) δ 0.8-0.9 (2d, 6H, 2×Leu-CH3), 1.4-1.6 (m, 2H, Leu-CH2), 2.06 (m, 1H, Leu-CH), 3.8 (s, 2H, CH2-Phe), 3.9 (d, 2H, CH2—SO2), 4.1 (m, 1H, α-H), 4.8 (t, 1H, CH═), 4.9-5.0 (b, 1H, NH), 5.1 (m, 2H, Cbz), 7.1-7.4 (m, 10H, 2×Ph), 7.5-7.7 (m, 5H, SO2-Ph); 8.4 (b, 1H, NH). MS (ESI) m/z 535 (M+1, 100%). Anal. calcd. for C30H34N2O5S: C, 67.39; H, 6.56; N, 5.43. Found: C, 67.12; H, 6.61; N, 5.33.

Sources & evidence

ORD record
ord-b85a075a517d4f0a88d8199dcf88b151
Source dataset
uspto-grants-2009_04
Patent number
US07521427B2

Reaction notes

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