Diisopropylethylamine → 5-{2-[4-(4-Ethoxymethyl-5-phenyl-oxazol-3-yl)-piperidin-1-yl]-ethyl}-2-methoxy-benzenesulfonamide

HRID 2288991ノート

反応式

HRID 2288991 の反応式
[CH2:1]([O:3][CH2:4][C:5]1[N:6]=[C:7](C2CCNCC2)[O:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:2].Cl[CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][C:28]([O:35][CH3:36])=[C:29]([S:31]([NH2:34])(=[O:33])=[O:32])[CH:30]=1.[NH2:37][C@H:38](C(O)=O)[CH2:39][C:40]1C=C2C(C=CC=C2)=[CH:42][CH:41]=1.CCN(C(C)C)C(C)C>O1CCOCC1>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH:40]2[CH2:39][CH2:38][N:37]([CH2:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([O:35][CH3:36])=[C:29]([S:31]([NH2:34])(=[O:33])=[O:32])[CH:30]=3)[CH2:42][CH2:41]2)[CH2:7][O:8][C:9]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH3:2]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 1859152-NaphthylalanineHCID 187004234-(4-Ethoxymethyl-5-phenyl-oxazol-2-yl)-piperidineHCID 187004435-(2-Chloroethyl)-2-methoxy-benzenesulfonamide

生成物 1

HCID 187004565-{2-[4-(4-Ethoxymethyl-5-phenyl-oxazol-3-yl)-piperidin-1-yl]-ethyl}-2-methoxy-benzenesulfonamide

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To 4-(4-ethoxymethyl-5-phenyl-oxazol-2-yl)-piperidine (0.150 g), prepared as in Intermediate 4, in dioxane is added 5-(2-chloro-ethyl)-2-methoxy-benzenesulfonamide (0.170 g), prepared as in Intermediate 1, Nal (0.012 g) and DIEA (0.274 ml). After heating at 100° C. for 18 hours, the reaction mixture is partitioned between EtOAc and dilute NaHCO3 solution. The organic phase is washed with saturated brine, dried (NaSO4) and concentrated. The residue is dissolved in 1:1 MeOH-CH2Cl2 and preadsorbed onto silica gel. Purification by flash chromatography on silica gel using a MeOH-EtOAc gradient (2-20%), affords the title compound as a white solid.

後処理

  1. customthe reaction mixture is partitioned between EtOAc and dilute NaHCO3 solution
  2. washThe organic phase is washed with saturated brine
  3. dry with materialdried (NaSO4)
  4. concentrationconcentrated
  5. dissolutionThe residue is dissolved in 1:1 MeOH-CH2Cl2
  6. customPurification by flash chromatography on silica gel using a MeOH-EtOAc gradient (2-20%)

出典と根拠

ORDレコード
ord-2dface9b081c491eaa426a2f50b929d1
出典データセット
uspto-grants-2000_07
特許番号
US06090825

反応ノート

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