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HRID75758

反应详情

EQUATION

反应方程式

HRID 75758 的结构方程式

REACTANTS

反应物

3
结构：ClCCl
HCID6344

Dichloromethane

CH2Cl2

结构：CC(C)OC(=O)Cl
HCID7917

Isopropyl chloroformate

C4H7ClO2

结构：COc1ccnc(C(=O)N[C@H]2COC[C@H](Cc3ccccc3)[C@@H](OCC(C)O)[C@H](C)OC2=O)c1O
HCID86701254

未命名化合物

PRODUCTS

生成物

1
结构：COc1ccnc(C(=O)N[C@H]2COC[C@H](Cc3ccccc3)[C@@H](OCC(C)C)[C@H](C)OC2=O)c1OC(=O)OC(C)C
HCID86701253

未命名化合物

收率 44%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CN(C)c1ccncc1
催化剂HCID14284

N,N-Dimethylpyridin-4-amine

C7H10N2

PROCEDURE

实验过程

To a solution of N-((3S,7S,8R,9S)-7-benzyl-8-(2-hydroxypropoxy)-9-methyl-2-oxo-1,5-dioxonan-3-yl)-3-hydroxy-4-methoxypicolinamide (160 mg, 0.33 mmol) in CH2Cl2 (2 mL) were added isopropyl chloroformate (44 mg, 0.36 mmol) and DMAP (44 mg, 0.36 mmol) at 0° C., and the solution was allowed to warm to room temperature overnight. The crude reaction mixture was concentrated and the residue purified via flash chromatography (SiO2, 50% EtOAc/hexanes) to furnish the product (83 mg, 44%) as white foam: IR (film) 3375, 2956, 2874, 1762, 1680 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.49 (d, J=8.4 Hz, 1H), 8.32 (d, J=5.4 Hz, 1H), 7.33-7.24 (m, 2H), 7.20 (dd, J=7.2, 5.3 Hz, 3H), 7.00 (d, J=5.5 Hz, 1H), 5.08-4.91 (m, 3H), 4.01 (dd, J=11.7, 7.4 Hz, 1H), 3.92 (s, 3H), 3.50-3.42 (m, 3H), 3.37-3.30 (m, 2H), 3.17-3.11 (m, 2H), 2.37-2.29 (m, 1H), 2.00-1.83 (m, 2H), 1.49 (d, J=6.4 Hz, 3H), 1.41 (d, J=6.3 Hz, 6H), 0.97-0.93 (m, 6H); 13C NMR (101 MHz, CDCl3) δ 171.79, 162.53, 159.38, 152.03, 146.81, 141.44, 140.03, 137.78, 129.20 (2), 128.43 (2), 126.09, 110.03, 84.53, 79.27, 75.68, 73.76, 72.31, 71.92, 56.32, 51.44, 47.43, 35.09, 29.19, 21.71 (2), 19.50 (2), 18.79; ESIMS m/z 574.39 ([M+H]+).

WORKUP

后处理

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. customthe residue purified via flash chromatography (SiO2, 50% EtOAc/hexanes)