Hydrochloric Acid → (S)-2-(4-Fluoro-3,5-dimethyl-benzyl)-4-{[3-(4-fluoro-phenyl)-propyl]-methyl-amino}-N-hydroxy-butyramide

HRID 1158146Notes

Reaction equation

HRID 1158146 reaction equation
C([C@@H]1COC(=O)[N:9]1[C:14](=[O:40])[C@@H:15]([CH2:30][C:31]1[CH:36]=[C:35]([CH3:37])[C:34]([F:38])=[C:33]([CH3:39])[CH:32]=1)[CH2:16][CH2:17][N:18]([CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[CH3:19])C1C=CC=CC=1.[C-]#N.[K+].Cl.C1C[O:48]CC1.CO>>[F:38][C:34]1[C:35]([CH3:37])=[CH:36][C:31]([CH2:30][C@@H:15]([CH2:16][CH2:17][N:18]([CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH3:19])[C:14]([NH:9][OH:48])=[O:40])=[CH:32][C:33]=1[CH3:39]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 21899815MeOH tetrahydrofuranHCID 68642196(R)-4-Benzyl-3-((S)-2-(4-fluoro-3,5-dimethyl-benzyl)-4-{[3-(4-fluoro-phenyl)-propyl]-methyl-amino}-butyryl)-oxazolidin-2-one

Product 1

HCID 86622006(S)-2-(4-Fluoro-3,5-dimethyl-benzyl)-4-{[3-(4-fluoro-phenyl)-propyl]-methyl-amino}-N-hydroxy-butyramideYield 66%

Procedure

To a solution of (R)-4-benzyl-3-((S)-2-(4-fluoro-3,5-dimethyl-benzyl)-4-{[3-(4-fluoro-phenyl)-propyl]-methyl-amino}-butyryl)-oxazolidin-2-one (0.033 g, 0.0601 mmol) in 2.5 mL of THF/MeOH/50% NH2OH—H2O (2:2:1), was added KCN (0.001 g, 0.006 mmol). After stirring at room temperature overnight, the reaction mixture was acidified with concentrated HCl to pH=2 and filtered. The product was isolated by RP-HPLC eluting with 20-100% acetonitrile (0.025% TFA)/water (0.025% TFA) to give the title compound as an off-white solid (0.016 g, 66% yield). LC-MS: tR=5.5 min, m/z 405 (M+H)+.

Workup

  1. filtrationfiltered
  2. customThe product was isolated by RP-HPLC
  3. washeluting with 20-100% acetonitrile (0.025% TFA)/water (0.025% TFA)

Sources & evidence

ORD record
ord-efd00d2336c04e0aa4be61066c03997c
Source dataset
uspto-grants-2010_10
Patent number
US07807720B2

Reaction notes

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