Potassium Hydroxide → {3-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-cyclopropylpyridin-3-yl]-4-methoxyphenyl}acetic acid

HRID 604674ノート

反応式

HRID 604674 の反応式
[F:1][C:2]([F:44])([F:43])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:27]=[C:28]([CH2:34][C:35]([O:37]C)=[O:36])[CH:29]=[CH:30][C:31]=4[O:32][CH3:33])=[CH:24][CH:23]=[C:22]([CH:39]4[CH2:41][CH2:40]4)[N:21]=3)[C@H:14]2[CH3:42])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH-].[K+]>CO>[F:44][C:2]([F:1])([F:43])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:27]=[C:28]([CH2:34][C:35]([OH:37])=[O:36])[CH:29]=[CH:30][C:31]=4[O:32][CH3:33])=[CH:24][CH:23]=[C:22]([CH:39]4[CH2:40][CH2:41]4)[N:21]=3)[C@H:14]2[CH3:42])[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 57576297methyl {3-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-cyclopropylpyridin-3-yl]-4-methoxyphenyl}acetate

生成物 1

HCID 24970135{3-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-cyclopropylpyridin-3-yl]-4-methoxyphenyl}acetic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of methyl {3-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-cyclopropylpyridin-3-yl]-4-methoxyphenyl}acetate (43 mg, 0.069 mmol) in MeOH (4 mL) was added 4M KOH (200 μL, 0.8 mmol). The reaction was stirred at room temperature for 4 hours and then quenched with HOAc (75 μL), diluted with EtOAc (30 μL), and washed with water and brine (10 mL each). The organic layer was dried (Na2SO4), filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (0 to 100% EtOAc/hexanes) afforded {3-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-cyclopropylpyridin-3-yl]-4-methoxyphenyl}acetic acid. LCMS=609.4 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 7.84 (s, 1H), 7.72 (s, 2H), 7.39 (d, J=7.8 Hz, 1H), 7.27 (m, 1H), 7.14 (d, J=7.8 Hz, 1H), 7.07 (bs, 1H), 6.93 (d, J=8.5 Hz, 1H), 5.53 (bs, 1H), 4.85 (d, J=16.0 Hz, 1H), 3.86-4.20 (m, 2H), 3.78 (s, 3H), 3.61 (s, 2H), 2.07 (m, 1H), 1.00-1.10 (m, 4H), 0.54-0.70 (m, 3H).

後処理

  1. customquenched with HOAc (75 μL)
  2. additiondiluted with EtOAc (30 μL)
  3. washwashed with water and brine (10 mL each)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by flash chromatography on silica gel (0 to 100% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-10ea2d24a3434b6b9708f746fcc43b6c
出典データセット
uspto-grants-2011_03
特許番号
US07910592B2

反応ノート

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