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

HRID 446421

반응식

HRID 446421 반응식
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

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 581685974-(2-Hydroxyethyl)phenethyl methanesulfonate2회HCID 66964182(2-Isopropylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b83e372cccba429ba151f23b5172a758
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476265B2

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