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HRID2111542

反应详情

EQUATION

反应方程式

HRID 2111542 的结构方程式

REACTANTS

反应物

4
结构：CC(C)(C)OO
HCID6410

tert-Butyl hydroperoxide

C4H10O2

结构：CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@H](C=CS(=O)(=O)C=C[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1)C(c1ccccc1)c1ccccc1)C(c1ccccc1)c1ccccc1
HCID86608592

未命名化合物

结构：CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@H](C=CS(=O)(=O)C=C[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(c1ccccc1)c1ccccc1)C(c1ccccc1)c1ccccc1
HCID86608595

未命名化合物

结构：[Li]CCCC
HCID178418339

Butyllithium

C4H9Li

PRODUCTS

生成物

1
结构：CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)NC(=CCS(=O)(=O)CC=C(NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(c1ccccc1)c1ccccc1)C(c1ccccc1)c1ccccc1
HCID86608594

未命名化合物

收率 21%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：C1CCOC1
溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

Cbz-Val-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-Val-Phe-AS-Ph as a white powder, yield 21%. 1H-NMR (CDCl3) δ 0.70-0.85 (2d, 6H, Val-CH3), 2.1 (m, 1H, Val-CH), 3.80 (d, 2H, CH2-Phe), 3.95 (m, 3H, CH2—SO2 and α-H), 4.90 (t, 1H, CH═), 5.12 (m, 3H, NH and Cbz), 7.1-7.4 (m, 10H, 2×Ph), 7.55 (t, 2H, SO2-Ph), 7.65 (t, 1H, SO2-Ph), 7.91 (d, 2H, SO2-Ph), 8.42 (b, 1H, NH). 13C NMR (300 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, 106.3, 67.6, 56.0, 55.6, 41.7, 22.0, 21.0, 18.4. MS (FAB+) m/z 521 (M+1, 100%). Anal. calcd. for C29H32N2O5S.1/10 H2O: C, 66.67; H, 6.21; N, 5.36. Found: C, 66.31; H, 6.23; N, 5.26.