Cyanogen Bromide → HCID 71009081, compound

HRID 1626095Notes

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 71008783HCID 71008783, compound

Product 1

HCID 71009081HCID 71009081, compoundYield 88%

Procedure

Starting from (1R,2R)-2-((R)-1-amino-2,2-difluoro-3-hydroxy-1-methyl-propyl)-cyclopropane-carboxylic acid ethyl ester (intermediate J5.2) the cyclization with cyanogen bromide yielded the (1R,2R)-2-((R)-2-amino-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-4-yl)-cyclopropanecarboxylic acid ethyl ester (88% yield) as a white solid. MS (ISP): m/z=263.2 [M+H]+.

Sources & evidence

ORD record: ord-79c7eab1425446e584c711fed0f64f2d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785436B2

Reaction notes

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