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HRID53067

反应详情

EQUATION

反应方程式

HRID 53067 的结构方程式

REACTANTS

反应物

4
结构：C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O)C[C@]2(C)[C@H]1C(=O)CO
HCID9053

Fluocortolone

C22H29FO4

结构：C(=NC1CCCCC1)=NC1CCCCC1
HCID10868

Dicyclohexylcarbodiimide

C13H22N2

结构：CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)O
HCID83693

L-Valine, N-[(1,1-dimethylethoxy)carbonyl]-

C10H19NO4

结构：CCCCCC.CCOC(C)=O
HCID21226206

未命名化合物

PRODUCTS

生成物

1
结构：CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OC(O)C(=O)[C@H]1[C@H](C)C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C
HCID131719962

未命名化合物

收率 46%

AUXILIARIES

试剂、催化剂与溶剂

2
结构：CN(C)c1ccncc1
催化剂HCID14284

N,N-Dimethylpyridin-4-amine

C7H10N2

结构：C1COCCO1.ClCCl
溶剂HCID18626912

未命名化合物

PROCEDURE

实验过程

26 mmol of fluocortolone (FC) is reacted with 32 mmol of Boc-valine (Boc-Val-OH), 2.9 mmol of 4-dimethylaminopyridine and 34 mmol of dicyclohexylcarbodiimide in dichloromethane/dioxane 3:2. Chromatography (ethyl acetate/hexane 2:1): F1 9.3 g of pure product, F2 4.8 g of slightly contaminated product. (Total yield 92%) crystallization of F1 from ethyl acetate/hexane yields 7.0 g (46%) of (2S)-2-((1,1-dimethylethoxycarbonyl)-amino)-3-methyl-butyric acid [11β,21-dihydroxy-6α-fluoro-16α-methyl-3,20-dioxo-pregna-1,4-dien-21-yl] ester.

WORKUP

后处理

  1. custom(Total yield 92%) crystallization of F1 from ethyl acetate/hexane