반응 #549625

ord-1f9f2fd8bbe14936b6a2b4d7689ccc8a

반응 방정식

CC(=O)OC(C)=O
acetic anhydride
COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)[C@@H](OC(C)=O)C[C@]4(C)[C@H]3[C@H](NCCC(C)C)C[C@]12C
Methyl 2β-acetoxy-3α-hydroxy-11α-(3-methylbutylamino)-5α-androstane-17β-carboxylate
Cc1ccc(S(=O)(=O)O)cc1
PTSA
→
COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](OC(C)=O)[C@@H](OC(C)=O)C[C@]4(C)[C@H]3[C@H](NCCC(C)C)C[C@]12C
oil
COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](OC(C)=O)[C@@H](OC(C)=O)C[C@]4(C)[C@H]3[C@H](NCCC(C)C)C[C@]12C
Methyl 2β,3α-diacetoxy-11α-(3-methylbutylamino)-5α-androstane-17β-carboxylate

반응물

CC(=O)OC(C)=O
acetic anhydride
COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)[C@@H](OC(C)=O)C[C@]4(C)[C@H]3[C@H](NCCC(C)C)C[C@]12C
Methyl 2β-acetoxy-3α-hydroxy-11α-(3-methylbutylamino)-5α-androstane-17β-carboxylate
Cc1ccc(S(=O)(=O)O)cc1
PTSA

시약

없음

용매

CCOC(C)=O
ethyl acetate
CCO
ethanol
ClC(Cl)Cl
chloroform

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    workup.WAITthe mixture left for 5 h
  2. 2
    기타evaporated
  3. 3
    기타to give an oil
  4. 4
    세척washed with aqueous ammonia solution (2×) and water (1×)
  5. 5
    기타dried
  6. 6
    기타evaporated

실험 절차

Methyl 2β-acetoxy-3α-hydroxy-11α-(3-methylbutylamino)-5α-androstane-17β-carboxylate (3.069 g) in chloroform (33 ml) containing dry PTSA (2.64 g) was stirred for 20 min then treated with acetic anhydride (6.5 ml) and the mixture left for 5 h. The mixture was diluted with ethanol and evaporated to give an oil. This was dissolved in ethyl acetate, washed with aqueous ammonia solution (2×) and water (1×), dried and evaporated to give an oil (2.867 g). This was purified by preparative t.l.c. in chloroform/methanol (9:1) to give the title compound [α]D +48.6°, νmax 1730 cm-1.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US04515786uspto-grants-1985_05