Cyanogen Bromide → HCID 71008637, compound

HRID 1626096Notes

Reaction equation

[CH2:1]([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C@:9]([NH2:16])([CH3:15])[C:10]([F:14])([F:13])[CH2:11][OH:12])=[O:5])[CH3:2].[N:17]#[C:18]Br>>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C@:9]1([CH3:15])[C:10]([F:14])([F:13])[CH2:11][O:12][C:18]([NH2:17])=[N:16]1)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 10476Cyanogen Bromide

HCID 71008696HCID 71008696, compound

Product 1

HCID 71008637HCID 71008637, compoundYield 61%

Procedure

Starting from (1S,2S)-2-((R)-1-amino-2,2-difluoro-3-hydroxy-1-methyl-propyl)-cyclopropane-carboxylic acid ethyl ester (intermediate J5.3) the cyclization with cyanogen bromide yielded the (1S,2S)-2-((R)-2-amino-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-4-yl)-cyclopropanecarboxylic acid ethyl ester (61% yield) as a white solid. MS (ISP): m/z=263.2 [M+H]+.

Sources & evidence

ORD record: ord-e6f26472893f45b28e3b15807324f0d7
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785436B2

Reaction notes

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