Hydrochloric Acid → HCID 68589874, compound

HRID 1028621Notes

Reaction equation

HRID 1028621 reaction equation
C(OC[N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[C@H:15]1[O:19][C:18](=[O:20])[N:17]([CH2:21][C:22]2[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:23]=2[C:32]2[CH:37]=[C:36]([CH:38]([CH3:40])[CH3:39])[C:35]([F:41])=[CH:34][C:33]=2[O:42][CH3:43])[C@H:16]1[CH3:44])C1C=CC=CC=1.Cl>CO.[OH-].[OH-].[Pd+2]>[F:41][C:35]1[C:36]([CH:38]([CH3:40])[CH3:39])=[CH:37][C:32]([C:23]2[CH:24]=[CH:25][C:26]([C:28]([F:31])([F:29])[F:30])=[CH:27][C:22]=2[CH2:21][N:17]2[C@@H:16]([CH3:44])[C@H:15]([C:11]3[NH:12][CH:13]=[CH:14][N:10]=3)[O:19][C:18]2=[O:20])=[C:33]([O:42][CH3:43])[CH:34]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66716667HCID 66716667, compound

Product 1

HCID 68589874HCID 68589874, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of (4S,5S)-5-{1-[(benzyloxy)methyl]-1H-imidazol-2-yl}-3-{[4′-fluoro-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one (EXAMPLE 244) (16.9 mg, 0.028 mmol), 20% palladium hydroxide on carbon (8.3 mg) and 1N HCl (28 uL) in MeOH (1 mL) was stirred under hydrogen (balloon) overnight, after which time it was filtered through Celite and concentrated in vacuo. The crude material was purified by flash chromatography to afford (4S,5R)-3-{[4′-fluoro-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-5-(1H-imidazol-2-yl)-4-methyl-1,3-oxazolidin-2-one. LCMS calc.=492.18; found=492.2 (M+1)+. 1H NMR (500 MHz, CDCl3, 1:1 mixture of atropisomers) δ 7.71 (s, 0.5 H); 7.67 (s, 0.5 H); 7.65 (s, 0.5 H); 7.64 (s, 0.5 H); 7.37 (d, J=3.2 Hz, 0.5 H); 7.35 (d, J=3.3 Hz, 0.5 H); 7.09 (d, 2 H); 7.02 (d, J=8.4 Hz, 0.5 H); 6.99 (d, J=8.5 Hz, 0.5 H); 6.72 (d, J=4.3 Hz, 0.5 H); 6.69 (d, J=4.2 Hz, 0.5H); 5.76 (d, J=8.3 Hz, 0.5 H); 5.64 (d, J=8.7 Hz, 0.5 H); 4.72 (d, J=15.8 Hz, 0.5 H); 4.68 (d, J=15.8 Hz, 0.5 H); 4.20 (d, J=15.7 Hz, 0.5 H); 4.01 (d, J=15.7 Hz, 0.5 H); 3.90 (br, s, 1H); 3.79-3.72 (m, 4H); 3.25-3.18 (m, 1 H); 1.28-1.22 (m, 6 H); 0.67 (d, J=6.5 Hz, 1.5 H); 0.59 (d, J=6.5 Hz, 1.5 H).

Workup

  1. filtrationafter which time it was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-63dd6e48d3e6410b9a79fb7762ddec55
Source dataset
uspto-grants-2014_05
Patent number
US08735435B2

Reaction notes

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