반응 #702371

ord-d729908d362f463ebe62f1d89d2af7b1

반응 방정식

COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)[C@@H](O)C[C@]4(C)[C@H]3[C@H](NCCC(C)C)C[C@]12C
Methyl 2β,3α-dihydroxy-11α-(3-methylbutylamino)5α-androstane-17β-carboxylate
Cl
hydrochloric acid
Cl
hydrochloric acid
→
CC(C)CCN[C@@H]1C[C@]2(C)[C@@H](C(=O)O)CC[C@H]2[C@@H]2CC[C@H]3C[C@H](O)[C@@H](O)C[C@]3(C)[C@H]21.Cl
foam
CC(C)CCN[C@@H]1C[C@]2(C)[C@@H](C(=O)O)CC[C@H]2[C@@H]2CC[C@H]3C[C@H](O)[C@@H](O)C[C@]3(C)[C@H]21.Cl
2β,3α-Dihydroxy-11α-(3-methylbutylamino)-5α-androstane-17β-carboxylic acid hydrochloride

반응물

COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)[C@@H](O)C[C@]4(C)[C@H]3[C@H](NCCC(C)C)C[C@]12C
Methyl 2β,3α-dihydroxy-11α-(3-methylbutylamino)5α-androstane-17β-carboxylate
Cl
hydrochloric acid
Cl
hydrochloric acid

시약

없음

용매

C1COCCO1
dioxan
O
water
O
water

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    온도heated on a steam bath for 5 days
  2. 2
    추출extracted with ethyl acetate (3×)
  3. 3
    세척The extracts were washed with brine
  4. 4
    기타dried
  5. 5
    기타evaporated

실험 절차

Methyl 2β,3α-dihydroxy-11α-(3-methylbutylamino)5α-androstane-17β-carboxylate (750 mg) in dioxan (20 ml) was treated with concentrated hydrochloric acid (3 ml) and water (10 ml) and heated on a steam bath for 5 days. The cooled mixture was diluted with water (200 ml) and acidified to pH 1 with dilute hydrochloric acid and extracted with ethyl acetate (3×). The extracts were washed with brine, dried and evaporated to give a foam (426 mg). This was purified by preparative t.l.c. in chloroform/methanol (4:1) to give the title compound (146 mg), [α]D +17° (in dimethyl sulphoxide).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US04497805uspto-grants-1985_02