تفاعل #93014

ord-8d75143b7589477eb7b0b8c2e8274815

معادلة التفاعل

CC(C)CC(O)C(=O)O
leucic acid
[Na+].[OH-]
NaOH
CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)CBr
16β-ethyl-17β-bromoacetoxy-4-estren-3-one
CN(C)C=O
DMF
→
CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)COC(=O)C(O)CC(C)C
above-identified compound
المردود 96.3%
CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)COC(=O)C(O)CC(C)C
16β-Ethyl-17β-(2-hydroxy-4-methylvaleryloxy)acetoxy-4-estren-3-one
المردود 96.3%

المتفاعلات

CC(C)CC(O)C(=O)O
leucic acid
[Na+].[OH-]
NaOH
CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)CBr
16β-ethyl-17β-bromoacetoxy-4-estren-3-one
CN(C)C=O
DMF

الكواشف

لا شيء

المذيبات

CC(C)=O
acetone

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.ADDITIONis added
  2. 2
    درجة الحرارةThe mixture is refluxed for 3 hours
  3. 3
    workup.ADDITIONtreated in the same manner as Example 26
  4. 4
    غسيلpassage of 50 ml of diisopropyl ether-n-hexane (1:1), elution
  5. 5
    أخرىThe eluate is evaporated under reduced pressure
  6. 6
    أخرىto remove the solvent

الإجراء التجريبي

In 2.0 ml of acetone is dissolved 0.26 g of leucic acid, and 1.0 ml of 2N-NaOH is added, followed by addition of 0.44 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 15 ml of DMF. The mixture is refluxed for 3 hours, and thereafter treated in the same manner as Example 26. The reaction mixture is then subjected to column chromatography. Following passage of 50 ml of diisopropyl ether-n-hexane (1:1), elution is carried out with 200 ml of diisopropyl ether. The eluate is evaporated under reduced pressure to remove the solvent, giving 0.475 g of the above-identified compound as a viscous oil.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04609650uspto-grants-1986_09