m-Chloroperbenzoic acid → HCID 178471788, compound

HRID 505301Notes

Reaction equation

HRID 505301 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[F:12][C:13]([F:55])([F:54])[C:14]1[CH:15]=[C:16]([C@H:24]2[O:28][C:27](=[O:29])[N:26]([CH2:30][C:31]3[C:36]([N:37]([CH2:40][C@H:41]4[CH2:46][CH2:45][C@H:44]([CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:43][CH2:42]4)[CH2:38][CH3:39])=[CH:35][CH:34]=[CH:33][N:32]=3)[C@H:25]2[CH3:53])[CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1>C(Cl)Cl>[F:55][C:13]([F:54])([F:12])[C:14]1[CH:15]=[C:16]([C@H:24]2[O:28][C:27](=[O:29])[N:26]([CH2:30][C:31]3[C:36]([N:37]([CH2:40][C@H:41]4[CH2:46][CH2:45][C@H:44]([CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:43][CH2:42]4)[CH2:38][CH3:39])=[CH:35][CH:34]=[CH:33][N+:32]=3[O-:9])[C@H:25]2[CH3:53])[CH:17]=[C:18]([C:20]([F:21])([F:22])[F:23])[CH:19]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178471785HCID 178471785, compound

Product 1

HCID 178471788HCID 178471788, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Chloroperbenzoic acid (77%, 120 mg, 0.486 mmol) was added to a solution of ethyl (trans-4-{[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)pyridin-3-yl](ethyl)amino]methyl}cyclohexyl)acetate (152.9 mg, 0.243 mmol) in dry CH2Cl2 (10 mL) at 0° C. under N2. After 15 min at 0° C., the reaction was stirred at room temperature for 5 h. The reaction mixture was diluted with CH2Cl2 (20 mL) and washed with saturated Na2SO3 (10 mL) and saturated K2CO3 (2×20 mL). The organic layers were dried (Na2SO4) and concentrated in vacuo to afford ethyl (trans-4-{[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-1-oxidopyridin-3-yl](ethyl)amino]methyl}cyclohexyl)acetate. LCMS calc.=646.3; found=646.3 (M+1)+.

Workup

  1. washwashed with saturated Na2SO3 (10 mL) and saturated K2CO3 (2×20 mL)
  2. dry with materialThe organic layers were dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e96c8387e24a41fcbea14cbf408f5f6a
Source dataset
uspto-grants-2010_08
Patent number
US07781426B2

Reaction notes

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