Chloroacetyl chloride → (R)-N-[1-(5-bromo-2-fluoro-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide

HRID 1946912Notes

Reaction equation

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

Participants

Reactant 2

HCID 6577Chloroacetyl chloride

HCID 58563010(R)-2-amino-2-(5-bromo-2-fluorophenyl)propan-1-ol

Product 1

HCID 66931512(R)-N-[1-(5-bromo-2-fluoro-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide

Procedure

In a manner analogous to that described for intermediate IX-1 the acylation of (R)-2-amino-2-(5-bromo-2-fluoro-phenyl)-propan-1-ol with chloro-acetyl chloride yielded the N—[(R)-1-(5-bromo-2-fluoro-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide as a light yellow oil (9.30 g, 90% of theory; e.e. >96%). MS (ISP): m/z=322.0 [M+H]+, 324.0 [M+2+H]+, 326.0 [M+4+H]+.

Sources & evidence

ORD record: ord-d19134928ea34ae08a9cbdb816936402
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399459B2

Reaction notes

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