تفاعل #2139974

ord-b067c2f186fa45adaaca11cd9a650512

معادلة التفاعل

CS(=O)(=O)Cl
Methanesulfonyl chloride
CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)O
N-(tert-butoxycarbonyl)-hydroxyproline
→
CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)OS(C)(=O)=O
O-mesyl N-(tert-butoxycarbonyl)-hydroxyproline

المتفاعلات

CS(=O)(=O)Cl
Methanesulfonyl chloride
CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)O
N-(tert-butoxycarbonyl)-hydroxyproline
—
TEA

الكواشف

لا شيء

المذيبات

ClCCl
DCM

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىto attain room temperature
  2. 2
    workup.STIRRINGwith continued stirring for an additional 45 minutes
  3. 3
    أخرىThe solvent was then evaporated
  4. 4
    استخلاصIt was extracted with ethyl acetate (twice) and the combined organic layer
  5. 5
    غسيلwas washed with brine
  6. 6
    تجفيفdried over sodium sulfate
  7. 7
    أخرىThe solvent was evaporated
  8. 8
    أخرىresidue dried under vacuum

الإجراء التجريبي

Methanesulfonyl chloride (2 eq) was slowly added at 0° C. to a DCM solution of N-(tert-butoxycarbonyl)-hydroxyproline N,O-dimethylhydroxamide and TEA (2 eq). The reaction mixture was stirred for an additional 10 minutes and allowed to attain room temperature with continued stirring for an additional 45 minutes. The solvent was then evaporated and residue taken in water. It was extracted with ethyl acetate (twice) and the combined organic layer was washed with brine and dried over sodium sulfate. The solvent was evaporated and residue dried under vacuum to give O-mesyl N-(tert-butoxycarbonyl)-hydroxyproline N,O-dimethylhydroxamide. The yield from this reaction.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07326707B2uspto-grants-2008_02