Water → HCID 23438587, compound

HRID 2120113Notes

Reaction equation

HRID 2120113 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][N:15]=1.Cl.CN(C)CCCN=C=NCC.O>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][N:15]=1)=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 706222-Amino-5-bromopyridineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 23438587HCID 23438587, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

In 100 ml of pyridine was dissolved 10.13 g of N-t-butoxycarbonylglycine and the solution was added with 5 g of 2-amino-5-bromopyridine, 13.85 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 7.06 g of 4-dimethylaminopyridine, individually at room temperature. Stirring was conducted for 15 hours at the same temperature. Water was added to the reaction mixture which was then extracted with ethyl acetate. The organic layer thus separated was washed with brine, dehydrated, filtered, and concentrated under vacuum to give 5.58 g of 2-(N-t-butoxycarbonylglycinylamino)-5-bromopyridine. This compound was dissolved, along with 5.82 g of (S)-[N-3-(4-trimethylstannyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl acetamide, in 70 ml of dimethylformamide and added with 4.9 ml of triethyl amine and 2.97 g of dichlorobistriphenylphosphine palladium (II) at room temperature. Reaction was performed at 100° C. for 4 hours with stirring. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with brine, dehydrated, filtered and concentrated under vacuum. Recrystallization of the concentrate provided 5.13 g of (S)-[N-3-(4-(2-(N-t-butoxycarbonylglycinylaminopyridin-5-yl)-3-fluorophenyl)-2-oxo-5-oxazolidinyl)methyl acetamide. This product was reacted with 1.65 ml of trimethylsilyl iodide in chloroform at room temperature for 30 min under a nitrogen atmosphere with stirring. Following the addition of chloroform, the organic layer thus separated was washed with brine, dehydrated, filtered, and concentrated in vacuo. The concentrate was purified through column chromatography to provide the title compound. 550 mg.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. customThe organic layer thus separated
  3. washwas washed with brine
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-11e64c3d5aa240c8849fc159daae06f5
Source dataset
uspto-grants-2004_02
Patent number
US06689779B2

Reaction notes

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