Water → 1-{4-[5-(2-Fluorobiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]benzyl}-piperidine-4,4-dicarboxylic acid benzyl ester (2,2-dimethyl-propanoyl-oxymethyl) ester

HRID 2407487ノート

反応式

HRID 2407487 の反応式
C(=O)([O-])[O-].[Na+].[Na+].[CH2:7]([O:14][C:15]([C:17]1([C:48]([OH:50])=[O:49])[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[N:34]=[C:33]([C:35]4[CH:40]=[CH:39][C:38]([C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)=[C:37]([F:47])[CH:36]=4)[O:32][N:31]=3)=[CH:26][CH:25]=2)[CH2:19][CH2:18]1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:51]([O:57][CH2:58]Cl)(=[O:56])[C:52]([CH3:55])([CH3:54])[CH3:53].O>CN(C)C(=O)C>[CH3:53][C:52]([CH3:55])([CH3:54])[C:51]([O:57][CH2:58][O:49][C:48]([C:17]1([C:15]([O:14][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:16])[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:25]=[CH:26][C:27]([C:30]3[N:34]=[C:33]([C:35]4[CH:40]=[CH:39][C:38]([C:41]5[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=5)=[C:37]([F:47])[CH:36]=4)[O:32][N:31]=3)=[CH:28][CH:29]=2)[CH2:19][CH2:18]1)=[O:50])=[O:56]

参加物

6

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 87885Chloromethyl pivalateHCID 595094311-{4-[5-(2-Fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}piperidine-4,4-dicarboxylic acid benzyl ester

生成物 1

HCID 595094441-{4-[5-(2-Fluorobiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]benzyl}-piperidine-4,4-dicarboxylic acid benzyl ester (2,2-dimethyl-propanoyl-oxymethyl) ester

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

Sodium carbonate (0.125 g, 0.0012 mol) is added to a solution of 1-{4-[5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazole-3-yl]benzyl}piperidine-4,4-dicarboxylic acid mono benzyl ester (0.35 g, 0.00059 mol) in N,N-dimethylacetamide (3.5 mL). The reaction mixture is stirred for 30 minutes at room temperature. Chloromethyl pivalate (0.187 g, 0.0012 mol) is added to the reaction mixture which is then heated at 65° C. for 4 hrs. The reaction mixture is treated with demineralized water (5 mL) and extracted in ethyl acetate (2×5 mL). Sodium chloride (0.25 g) is added to the ethyl acetate layer and stirred for 15 minutes. Demineralized water (5 mL) is added to the ethyl acetate layer and the layers are separated. The ethyl acetate layer is dried over sodium sulphate. Removal of solvent under reduced pressure gives a viscous liquid, which is purified by column chromatography (silica gel 230-400 mesh, n-hexane:ethyl acetate 70:30) to furnish 1-{4-[5-(2-fluorobiphenyl-4-yl)-1,2,4oxadiazol-3-yl]benzyl}-piperidine-4,4-dicarboxylic acid benzyl ester (2,2-dimethylpropanoyloxymethyl) ester.

後処理

  1. temperatureis then heated at 65° C. for 4 hrs
  2. extractionextracted in ethyl acetate (2×5 mL)
  3. additionSodium chloride (0.25 g) is added to the ethyl acetate layer
  4. stirringstirred for 15 minutes
  5. additionDemineralized water (5 mL) is added to the ethyl acetate layer
  6. customthe layers are separated
  7. dry with materialThe ethyl acetate layer is dried over sodium sulphate
  8. customRemoval of solvent under reduced pressure
  9. customgives a viscous liquid, which
  10. customis purified by column chromatography (silica gel 230-400 mesh, n-hexane:ethyl acetate 70:30)

出典と根拠

ORDレコード
ord-5f900c5b2b444d98b9bae977d7f6d417
出典データセット
uspto-grants-2014_08
特許番号
US08809539B2

反応ノート

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