Potassium Carbonate → (9-(4-(2-Hydroxyethyl)phenethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

HRID 446421

反応式

HRID 446421 の反応式
C(=O)([O-])[O-].[K+].[K+].FC(F)(F)C(O)=O.[CH:14]([C:17]1[S:18][CH:19]=[C:20]([C:22]([N:24]2[CH2:29][C:28]3([CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[O:27][CH2:26][CH2:25]2)=[O:23])[N:21]=1)([CH3:16])[CH3:15].CS([O:39][CH2:40][CH2:41][C:42]1[CH:47]=[CH:46][C:45]([CH2:48][CH2:49]O)=[CH:44][CH:43]=1)(=O)=O>C(#N)C.O>[OH:39][CH2:40][CH2:41][C:42]1[CH:47]=[CH:46][C:45]([CH2:48][CH2:49][N:32]2[CH2:31][CH2:30][C:28]3([O:27][CH2:26][CH2:25][N:24]([C:22]([C:20]4[N:21]=[C:17]([CH:14]([CH3:16])[CH3:15])[S:18][CH:19]=4)=[O:23])[CH2:29]3)[CH2:34][CH2:33]2)=[CH:44][CH:43]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 581685974-(2-Hydroxyethyl)phenethyl methanesulfonate2 回HCID 66964182(2-Isopropylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate

生成物 1

HCID 58168559(9-(4-(2-Hydroxyethyl)phenethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

Potassium carbonate (0.634 g) was added to a solution of (2-isopropylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate [Example 1, step b] (0.971 g) and 4-(2-hydroxyethyl)phenethyl methanesulfonate [Aromatic Intermediate 10] (0.56 g) in acetonitrile (20 mL) and water (0.3 mL). The reaction mixture was heated at 60° C. for 1 day. The solvent was evaporated under reduced pressure and the residue partitioned between water and ethyl acetate. The aqueous layer was re-extracted with ethyl acetate and the combined organic phases were dried, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography, using 2% methanol in dichloromethane with 1% triethylamine as solvent. Fractions containing the product were evaporated to dryness to afford the subtitled compound. Yield 0.68 g.

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue partitioned between water and ethyl acetate
  3. extractionThe aqueous layer was re-extracted with ethyl acetate
  4. customthe combined organic phases were dried
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customThe crude product was purified by flash silica chromatography
  8. additionFractions containing the product
  9. customwere evaporated to dryness

出典と根拠

ORDレコード
ord-b83e372cccba429ba151f23b5172a758
出典データセット
uspto-grants-2013_07
特許番号
US08476265B2

関連ノート

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