Water → 8-(4-(4-Methoxyphenyl)-5-(p-tolyl)thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 1802537

反応式

HRID 1802537 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH:21]3[CH2:30][CH2:29][C:24]4([O:28][CH2:27][CH2:26][O:25]4)[CH2:23][CH2:22]3)[S:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.C1(C2[O:39]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1.O>O1CCCC1.C([Li])CCC.CCCCCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([C:21]3([OH:39])[CH2:30][CH2:29][C:24]4([O:28][CH2:27][CH2:26][O:25]4)[CH2:23][CH2:22]3)[S:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1

参加物

7

反応物 3

HCID 962WaterHCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 672963928-(4-(4-Methoxyphenyl)-5-(p-tolyl)thiazol-2-yl)-1,4-dioxaspiro[4.5]decane

生成物 1

HCID 672964248-(4-(4-Methoxyphenyl)-5-(p-tolyl)thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol収率 55%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒HCID 178418339Butyllithium溶媒

実験手順

To a solution of 8-(4-(4-methoxyphenyl)-5-(p-tolyl)thiazol-2-yl)-1,4-dioxaspiro[4.5]decane (Reference Example 95) (734 mg, 1.74 mmol) in tetrahydrofuran (8.7 mL), 1.63 M n-butyllithium/solution in n-hexane (1.17 mL) was added at −78° C., and the obtained solution was stirred at the same temperature for 1 hour. The reaction solution was added at −78° C. to a solution of 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine (546 mg, 2.09 mmol) in tetrahydrofuran (8.7 mL), and the obtained solution was allowed to warm gradually to room temperature with stirring. Distilled water was added to the reaction solution, and the resulting solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate) to obtain the captioned compound (417 mg, 0.954 mmol, 55%) as a colorless amorphous product.

後処理

  1. stirringwith stirring
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-12da87406791480d8fa40e1474ed09bd
出典データセット
uspto-grants-2013_01
特許番号
US08349874B2

関連ノート

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