반응 #812441

ord-6280d3e33d7e42d29f4bb246ba4d1112

반응 방정식

N=C(N)NN.O=C(O)O
aminoguanidine hydrogencarbonate
Cl
HCl
C/C(C=O)=C\[C@H]1CC[C@]2(O)[C@@H]3CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
(E)-3β,14β-dihydroxy-21-methyl-5β-pregn-20-ene-21-carboxaldehyde
→
CC(/C=N/NC(=N)N)=C\[C@H]1CC[C@]2(O)[C@@H]3CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
title compound
수율 68.3%
CC(/C=N/NC(=N)N)=C\[C@H]1CC[C@]2(O)[C@@H]3CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
(E,E)-17β-(3-Guanidinoimino-2-methyl-1-propenyl)-5β-androstane-3β,14β-diol
수율 68.3%

반응물

N=C(N)NN.O=C(O)O
aminoguanidine hydrogencarbonate
Cl
HCl
C/C(C=O)=C\[C@H]1CC[C@]2(O)[C@@H]3CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
(E)-3β,14β-dihydroxy-21-methyl-5β-pregn-20-ene-21-carboxaldehyde

시약

없음

용매

O
water
C1COCCO1
dioxane
C1COCCO1
dioxane

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타After 3 days the mixture was evaporated to dryness under reduced pressure
  2. 2
    기타The crude product was purified by flash chromatography (SiO2)
  3. 3
    workup.ADDITIONthe fractions containing the title compound
  4. 4
    기타were collected
  5. 5
    기타evaporated to dryness

실험 절차

A mixture of 0.50 g of aminoguanidine hydrogencarbonate in 10 ml of water and 30 ml of dioxane was made acid to pH 3 with 3N HCl. A solution of 0.95 g of (E)-3β,14β-dihydroxy-21-methyl-5β-pregn-20-ene-21-carboxaldehyde (Prepn. 1) in 10 ml of dioxane was added at room temperature. After 3 days the mixture was evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography (SiO2) using chloroform/methanol/28% ammonium hydroxide 80/20/3 as the eluant: the fractions containing the title compound were collected and evaporated to dryness. The residue was ground with diethyl ether and ethanol to give 0.75 g of the title compound (I-aa) as a white solid.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05705662uspto-grants-1998_01