반응 #1914844

ord-81b7f41bd552435aa8af498604c46520

반응 방정식

O=C(Cl)CCCCl
4-chlorobutanoylchloride
C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO
hydrocortisone
→
C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO.O=C([O-])CCCCl
Hydrocortisone (4-chloro)butanoate
수율 53.0%

반응물

O=C(Cl)CCCCl
4-chlorobutanoylchloride
C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO
hydrocortisone

시약

없음

용매

CCN(CC)CC
triethylamine

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    건조dried over P2O5
  2. 2
    workup.ADDITIONThe solution was treated with water
  3. 3
    기타the organic phase was separated
  4. 4
    건조dried (Na2SO4)
  5. 5
    기타to give a white solid with a 53% yield by weight, which
  6. 6
    기타a melting point (m.p.) of 155° C.

실험 절차

4 portions of 4-chlorobutanoylchloride (0.32 ml×4) and triethylamine (0.3 g×4) were added in 24 hours to a solution of hydrocortisone (1 g) in CHCl, dried over P2O5 and stirred for 3 days. The solution was treated with water, the organic phase was separated, dried (Na2SO4) and deprived of the solvent at reduced pressure. The crude residue was ground with hexane and CH2Cl2 to give a white solid with a 53% yield by weight, which had a melting point (m.p.) of 155° C.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07056905B2uspto-grants-2006_06