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HRID1873247

反应详情

EQUATION

反应方程式

HRID 1873247 的结构方程式

REACTANTS

反应物

4
结构：ClCCCl
HCID11

1,2-Dichloroethane

C2H4Cl2

结构：On1nnc2ccccc21
HCID75771

1-Hydroxybenzotriazole

C6H5N3O

结构：COC(=O)N[C@H](C(=O)N[C@@H](Cc1ccccc1)[C@@H](O)CN(N)Cc1ccc(-c2cncs2)cc1)C(C)C
HCID10768426

未命名化合物

结构：COC(=O)N[C@H](C(=O)O)C(C)(C)C
HCID11263950

N-(Methoxycarbonyl)-3-methyl-L-valine

C8H15NO4

PRODUCTS

生成物

1
结构：COC(=O)N[C@H](C(=O)N[C@@H](Cc1ccccc1)[C@@H](O)CN(Cc1ccc(-c2cncs2)cc1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C(C)C
HCID467947

2,5,6,10,13-Pentaazatetradecanedioic acid, 3-(1,1-dimethylethyl)-8-hydroxy-12-(1-methylethyl)-4,11-dioxo-9-(phenylmethyl)-6-((4-(5-thiazolyl)phenyl)methyl)-, dimethyl ester, (3S,8S,9S,12S)-

C35H48N6O7S

AUXILIARIES

试剂、催化剂与溶剂

3
结构：O
溶剂HCID962

Water

H2O

结构：CN(C)C=O
溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

结构：CCOC(C)=O
溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

Under argon, 213 mg (1.13 mmol) of N-methoxycarbonyl-(L)-tert-leucine (Example 2e), 431 mg (2.25 mmol) of EDC and 304 mg (2.25 mmol) of HOBT are placed in 18 ml of DMF. After 15 min, 627 μl (4.5 mmol) of TEA and 0.75 mmol of 1-[4-(thiazol-5-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-valyl)amino-6-phenyl-2-azahexane are added. After 2 hours, water and ethyl acetate are added; the aqueous phase is separated off and extracted a further 2× with ethyl acetate. The organic phases are washed 2× with water, sat. NaHCO3 solution, 2× water and brine, dried (Na2SO4) and concentrated by evaporation. Column chromatography (SiO2 ; methylene chloride/THF 5:1) and crystallisation from ether yield the title compound: m.p: 200-201° C.; HPLC20-100 : tRet =14.0; FAB MS (M+H)+ =697.

WORKUP

后处理

  1. waitAfter 2 hours
  2. customthe aqueous phase is separated off
  3. extractionextracted a further 2× with ethyl acetate
  4. washThe organic phases are washed 2× with water, sat. NaHCO3 solution, 2× water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated by evaporation
  7. customColumn chromatography (SiO2 ; methylene chloride/THF 5:1) and crystallisation from ether