Hydrochloric Acid → HCID 54585907, compound

HRID 1158140Notes

Reaction equation

HRID 1158140 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][CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[C:24]([CH3:29])[CH:23]=1)C1C=CC=CC=1.[C-]#N.[K+].Cl.C1C[O:48]CC1.CO>>[OH:48][NH:9][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][CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[C:24]([CH3:29])[CH:23]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 21899815MeOH tetrahydrofuranHCID 68642198HCID 68642198, compound

Product 1

HCID 54585907HCID 54585907, compoundYield 18%

Procedure

To a solution of (R)-4-Benzyl-3-[(S)-2-(4-fluoro-3,5-dimethyl-benzyl)-8-(4-fluoro-3-methyl-phenyl)-octanoyl]-oxazolidin-2-one (0.036 g, 0.0657 mmol) in 2.5 mL of THF/MeOH/50% NH2OH—H2O (2:2:1), was added KCN (0.001 g, 0.007 mmol). After stirring at room temperature for 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 (0.005 g, 18% yield). LC-MS: tR=11.1 min, m/z 404 (M+H)+; 1H NMR (300 MHz, CD3OD) δ 1.21-1.33 (m, 6H), 1.34-1.48 (m, 2H), 1.49-1.66 (m, 2H), 2.18 (s, 6H), 2.21 (s, 3H), 2.23-2.32 (m, 1H), 2.51 (t, J=7.32 Hz, 2H), 2.56-2.62 (m, 1H), 2.67-2.78 (m, 1H), 6.81 (d, J=6.74 Hz, 2H), 6.88 (t, J=9.37 Hz, 1H), 6.91-6.97 (m, 1H), 7.00 (d, J=7.03 Hz, 1H).

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-14d66826d481421890189f307ab207e4
Source dataset
uspto-grants-2010_10
Patent number
US07807720B2

Reaction notes

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