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HRID1008997

反应详情

EQUATION

反应方程式

HRID 1008997 的结构方程式

REACTANTS

反应物

3
结构：Cl
HCID313

Hydrochloric Acid

ClH

2 次

结构：COCn1c(-c2ccccc2O)c(C2CCCCC2)c2sc(C(=O)OC)c(C)c21
HCID67298636

未命名化合物

结构：CC1(C)OC[C@H](COS(=O)(=O)c2ccc([N+](=O)[O-])cc2)N1C(=O)OCc1ccccc1
HCID86629786

Phenylmethyl (4R)-2,2-dimethyl-4-[[[(4-nitrophenyl)sulfonyl]oxy]methyl]-3-oxazolidinecarboxylate

C20H22N2O8S

PRODUCTS

生成物

1
结构：COC(=O)c1sc2c(C3CCCCC3)c(-c3ccccc3OC[C@@H](CO)NC(=O)OCc3ccccc3)[nH]c2c1C
HCID67298563

未命名化合物

收率 31%

AUXILIARIES

试剂、催化剂与溶剂

3
结构：CO
溶剂HCID887

Methanol

CH4O

2 次

结构：CN(C)C=O
溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

结构：C1COCCO1
溶剂HCID31275

1,4-Dioxane

C4H8O2

CONDITIONS

反应条件

温度
50 °C

PROCEDURE

实验过程

Methyl 6-cyclohexyl-5-(2-hydroxyphenyl)-4-(methoxymethyl)-3-methyl-4H-thieno[3,2-b]pyrrole-2-carboxylate was dissolved in dioxane (0.036M) and the same volume of 6N HCl was added. The mixture was subjected to microwave irradiation (10 min @ 130° C.). All volatiles were evaporated and the product was enriched by prep. RP-HPLC. The product-containing fractions were lyophilised to give a green glassy solid. This material was dissolved in DMF (0.16M) and benzyl (4R)-2,2-dimethyl-4-({[(4-nitrophenyl)sulfonyl]oxy}methyl)-1,3-oxazolidine-3-carboxylate (excess, prepared according to Synthesis 1996, 189 in analogy to benzyl (4R)-2,2-dimethyl-4-({[(4-methylphenyl)sulfonyl]oxy}methyl)-1,3-oxazolidine-3-carboxylate from benzyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate and substituting tosyl chloride with 4-nitrobenzenesulfonyl chloride) was added. The suspension was heated to 50° C. overnight. All volatiles were evaporated i. vac. and the residual material was purified by prep. RP-HPLC. The product fractions were evaporated and the residual material lyophilised from MeCN/water. A beige solid was obtained, which was dissolved dry MeOH (0.2M) and 1.25M HCl in MeOH (excess) was added. The solution was left stirring at RT. After 3 h all volatiles were evaporated and the residual material was subjected to purification by chromatography (PE:EtOAc, 6:4). After evaporation of the product fractions the product was obtained as a yellow powder (31%). MS (ES+) m/z 577 (M+H)+.

WORKUP

后处理

  1. customThe mixture was subjected to microwave irradiation (10 min @ 130° C.)
  2. customAll volatiles were evaporated
  3. customto give a green glassy solid
  4. customAll volatiles were evaporated i
  5. customand the residual material was purified by prep
  6. customThe product fractions were evaporated
  7. customA beige solid was obtained
  8. additionwas added
  9. waitThe solution was left
  10. customAfter 3 h all volatiles were evaporated
  11. customthe residual material was subjected to purification by chromatography (PE:EtOAc, 6:4)
  12. customAfter evaporation of the product fractions the product