N,O-Dimethylhydroxylamine → HCID 86591229, compound

HRID 132797Notes

Reaction equation

HRID 132797 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:19]([OH:21])=O)[CH2:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CNOC.[CH:26]1C=CC2N(O)N=NC=2[CH:31]=1.C([Mg]Br)=C>CN(C=O)C.C1COCC1>[F:17][C:15]1[CH:16]=[C:11]([CH:12]=[C:13]([F:18])[CH:14]=1)[CH2:10][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:19](=[O:21])[CH:26]=[CH2:31]

Participants

7

Reactant 4

HCID 14232N,O-DimethylhydroxylamineHCID 757711-HydroxybenzotriazoleHCID 27790093,5-Difluoro-L-phenylalanine, N-BOC protectedHCID 178418507HCID 178418507, compound

Product 1

HCID 86591229HCID 86591229, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.).

Sources & evidence

ORD record
ord-e2a749681a1d4191907388b7b1f41bae
Source dataset
uspto-grants-2008_06
Patent number
US07388118B2

Reaction notes

Loading…