Sodium Hydroxide → HCID 58155226, compound

HRID 920139Notes

Reaction equation

HRID 920139 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([C:8]2([CH3:15])[NH:12]C(=O)N[C:9]2=[O:14])[CH:7]=1.[OH-].[Na+].NC(C1C=C(Br)C=CC=1F)(C)[C:21](O)=[O:22].S(Cl)(Cl)=O>CO>[CH3:21][O:22][C:9](=[O:14])[C:8]([NH2:12])([C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:16])[CH3:15]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 666318422-amino-2-(5-bromo-2-fluorophenyl)propanoic acidHCID 66931525HCID 66931525, compound

Product 1

HCID 58155226HCID 58155226, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The hydrolysis of the (RS)-5-(5-bromo-2-fluoro-phenyl)-5-methyl-imidazolidine-2,4-dione with 6 N sodium hydroxide solution and esterification of the resulting (RS)-2-amino-2-(5-bromo-2-fluoro-phenyl)-propionic acid with methanol and thionylchloride yielded the (RS)-2-amino-2-(5-bromo-2-fluoro-phenyl)-propionic acid methylester as a light yellow oil. The purity of the product allowed using it in the next step without further purification. Mass (calculated) C10H11BrFNO2 [276.107]; (found) [M+H]+=276, 278.

Sources & evidence

ORD record
ord-f6cdc04ba3734eee8a5ff6be8a1956a6
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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