تفاعل #219979

ord-e2a749681a1d4191907388b7b1f41bae

معادلة التفاعل

On1nnc2ccccc21
HOBT
CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)C(=O)O
N-(tert-butoxycarbonyl)-3,5-difluoro-L-phenylalanine
CNOC
N-methyl-N-methoxylamine
C=[CH][Mg][Br]
vinylmagnesium bromide
→
C=CC(=O)[C@H](Cc1cc(F)cc(F)c1)NC(=O)OC(C)(C)C
vinyl ketone
C=CC(=O)[C@H](Cc1cc(F)cc(F)c1)NC(=O)OC(C)(C)C
Tert-butyl (1S)-1-(3,5-difluorobenzyl)-2-oxobut-3-enylcarbamate

المتفاعلات

On1nnc2ccccc21
HOBT
CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)C(=O)O
N-(tert-butoxycarbonyl)-3,5-difluoro-L-phenylalanine
CNOC
N-methyl-N-methoxylamine
—
amide
C=[CH][Mg][Br]
vinylmagnesium bromide
—
carbodimide EDC

الكواشف

لا شيء

المذيبات

CN(C)C=O
DMF
C1CCOC1
THF

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

الإجراء التجريبي

N-(tert-butoxycarbonyl)-3,5-difluoro-L-phenylalanine (1) is coupled to N-methyl-N-methoxylamine using the carbodimide EDC in the presence of HOBT in DMF. The “Weinreb” amide product (m.p. 48° C.) is then treated with vinylmagnesium bromide in THF at 0° C. for 2 hr. Workup provided vinyl ketone 2 (m.p. 115° C.).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07388118B2uspto-grants-2008_06