تفاعل #2045117

ord-5713ec8692ef47d097eebbfd1e544e5e

معادلة التفاعل

Cl
HCl
[Na+].[OH-]
NaOH
COC(=O)C(C)C[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
Methyl 23-methyl-3α,7α-dihydroxy-5β-cholan-24-oate
→
C[C@H](C[C@H](C)C(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
23(S)-Methyl-3α,7α-dihydroxy-5β-cholan-24-oic acid
المردود 65.0%
C[C@H](C[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(=O)O
23(R)-Methyl-3α,7α-dihydroxy-5β-cholan-24-oic acid

المتفاعلات

Cl
HCl
[Na+].[OH-]
NaOH
COC(=O)C(C)C[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
Methyl 23-methyl-3α,7α-dihydroxy-5β-cholan-24-oate

الكواشف

لا شيء

المذيبات

CO
MeOH
CO
MeOH

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةThe mixture was refluxed for 16 h
  2. 2
    استخلاصextracted with EtOAc (3×20 mL)
  3. 3
    غسيلThe combined organic fractions were washed with brine (1×50 mL)
  4. 4
    تجفيفdried (Na2SO4)
  5. 5
    أخرىevaporated under vacuum
  6. 6
    أخرىThe residue was purified by silica gel flash chromatography
  7. 7
    غسيلElution with CHCl3

الإجراء التجريبي

Methyl 23-methyl-3α,7α-dihydroxy-5β-cholan-24-oate 0.97 g (2.3 mmol) was dissolved in MeOH (25 mL) and added with 10% NaOH in MeOH (5.7 mL, 14.2.mmol). The mixture was refluxed for 16 h. The mixture was acidified with 3N HCl and extracted with EtOAc (3×20 mL). The combined organic fractions were washed with brine (1×50 mL), dried (Na2SO4) and evaporated under vacuum. The residue was purified by silica gel flash chromatography. Elution with CHCl3:MeOH (95/5) afforded 1.5 g (65%) of 23(S)-Methyl-3α,7α-dihydroxy-5β-cholan-24-oic acid and 330 mg of 23(R)-Methyl-3α,7α-dihydroxy-5β-cholan-24-oic acid.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08410083B2uspto-grants-2013_04