Sodium borohydride → (S)-N-[[3-[3-Fluoro-4-(4-(1-hydroxyethyl)-1H-1,2,3-triazol-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 1415901Notes

Reaction equation

HRID 1415901 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][C@H:13]([CH2:15][NH:16][C:17](=[O:19])[CH3:18])[O:12][C:11]2=[O:20])=[CH:6][C:5]=1[F:21])=[N+:2]=[N-:3].[BH4-].[Na+].[CH2:24]1[CH2:28]O[CH2:26][CH2:25]1.C[OH:30]>>[F:21][C:5]1[CH:6]=[C:7]([N:10]2[CH2:14][C@H:13]([CH2:15][NH:16][C:17](=[O:19])[CH3:18])[O:12][C:11]2=[O:20])[CH:8]=[CH:9][C:4]=1[N:1]1[CH:26]=[C:25]([CH:24]([OH:30])[CH3:28])[N:3]=[N:2]1

Participants

4

Reactant 3

HCID 4311764Sodium borohydrideHCID 10708829(S)-N-[[3-[4-Azido-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamideHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 53715128(S)-N-[[3-[3-Fluoro-4-(4-(1-hydroxyethyl)-1H-1,2,3-triazol-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamideYield 80%

Procedure

A solution of 150 mg (0.40 mmol) of the compound of Example 17 in 10 mL 1:1 THF-methanol was treated with 15 mg (0.4 mmol) of sodium borohydride followed by stirring at ambient temperature for 18 h. The mixture was concentrated in vacuo, dissolved in 1:1 methanol-dichloromethane and filtered. The filtrate was concentrated in vacuo and the residue was subjected to radial chromatography on a 2 mm chromatotron plate. These procedures afforded 120 mg (80%) of the title compound as a white solid. Mass Spectrum (EI): m/z 363, 291, 276, 232, 217, 207, 191, 179, 163, 148, 135, 123, 85, 56.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutiondissolved in 1:1 methanol-dichloromethane
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-98081b6721924359a1fe5a6e3b67a51e
Source dataset
uspto-grants-1999_06
Patent number
US05910504

Reaction notes

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