3-Chlorobenzoic Acid → HCID 11526443, compound

HRID 1994592Notes

Reaction equation

HRID 1994592 reaction equation
ClC1C=C(C=CC=1)C(O)=[O:6].[F:11][C:12]1[C:17]([CH:18]([CH3:20])[CH3:19])=[CH:16][C:15]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=2[CH2:31][N:32]2[C@@H:36]([CH3:37])[C@@H:35]([C:38]3[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=3)[O:34][C:33]2=[O:44])=[C:14]([O:45][CH3:46])[CH:13]=1>C(Cl)Cl>[F:11][C:12]1[C:17]([CH:18]([CH3:19])[CH3:20])=[CH:16][C:15]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:28])[F:29])=[CH:23][C:22]=2[CH2:31][N:32]2[C@@H:36]([CH3:37])[C@@H:35]([C:38]3[CH:43]=[CH:42][N+:41]([O-:6])=[CH:40][CH:39]=3)[O:34][C:33]2=[O:44])=[C:14]([O:45][CH3:46])[CH:13]=1

Participants

4

Reactant 2

HCID 4473-Chlorobenzoic AcidHCID 11684781HCID 11684781, compound

Product 1

HCID 11526443HCID 11526443, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

m-Chlorobenzoic acid (77%, 47.9 mg, 0.214 mmol) was added to a solution of (4S,5R)-3-{[4′-fluoro-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-5-pyridin-4-yl-1,3-oxazolidin-2-one (53.7, 0.107 mmol) in dry CH2Cl2 (10.8 mL) at 0° C. After 15 min at 0° C., the reaction was stirred at room temperature for 3 h. The reaction was diluted with CH2Cl2 (40 mL) and washed with saturated Na2SO3 (20 mL) and saturated K2CO3 (2×20 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo to afford (4S,5R)-3-{[4′-fluoro-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-5-(1-oxidopyridin-4-yl)-1,3-oxazolidin-2-one as an oil. LCMS calc.=519.2; found=519.3 (M+1)+.

Workup

  1. washwashed with saturated Na2SO3 (20 mL) and saturated K2CO3 (2×20 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ed5e671af9a246759a689f1ca577db65
Source dataset
uspto-grants-2010_01
Patent number
US07652049B2

Reaction notes

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