反応 #1914844

ord-81b7f41bd552435aa8af498604c46520

反応方程式

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
収率 53.0%

反応物

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

試薬

なし

溶媒

CCN(CC)CC
triethylamine

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

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

実験手順

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.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US07056905B2uspto-grants-2006_06