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

HRID 2111543Notes

Reaction equation

HRID 2111543 reaction equation
[C:1]1([CH:7]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)[C@H:8]([NH:46][C:47](=[O:61])[C@H:48]([CH3:60])[NH:49][C:50]([O:52][CH2:53][C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)=[O:51])[CH:9]=[CH:10][S:11]([CH:14]=[CH:15][C@@H:16]([NH:30][C:31](=[O:45])[C@H:32]([CH3:44])[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:45])[C@H:32]([CH3:44])[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:46][C:47](=[O:61])[C@H:48]([CH3:60])[NH:49][C:50]([O:52][CH2:53][C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=2)=[O:51])[CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:62]2[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=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 86608597HCID 86608597, compoundHCID 178418339Butyllithium

Product 1

HCID 86608596Phenyl-3-(N-carbobenzyloxyalanyl)amino-4-phenylbut-2-enyl SulfoneYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cbz-Ala-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-Ala-Phe-AS-Ph as a white powder, yield 93%. 1H-NMR (CDCl3) δ 1.21 (d, 3H, Ala-CH3), 3.80 (m, 4H, CH2-Phe and CH2—SO2), 4.12 (q, 1H, α-H), 4.88 (t, 1H, CH═), 5.11 (m, 3H, NH and Cbz), 7.30 (m, 10H, 2×Ph), 7.50 (t, 2H, SO2-Ph), 7.64 (t, 1H, SO2-Ph), 7.83 (d, 2H, SO2-Ph), 8.40 (b, 1H, NH). 13C NMR (400 MHz, CDCl3) δ 172.1, 156.3, 144.4, 140.8, 135.7, 134.2, 133.6, 131.2, 129.5, 129.4×2, 129.3, 128.8×2, 128.7, 128.6, 128.4, 128.3, 127.8, 127.3, 126.9, 107.2, 67.6, 51.7, 51.6, 40.2, 19.4. MS (FAB+) m/z 493 (M+1, 100%). HRMS calcd. for C27H29N2O5S: 493.17972. Obsd. 493.17663. Anal. calcd. for C27H28N2O5S: C, 65.83; H, 5.73; N, 5.69. Found: C, 65.73; H, 5.82; N, 5.68.

Sources & evidence

ORD record
ord-d320442096934e888f099a9b517c5300
Source dataset
uspto-grants-2009_04
Patent number
US07521427B2

Reaction notes

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