Triethylamine → 3-{4-[3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-3-hydroxy-butyryl]-phenyl}-3-fluoro-azetidine-1-carboxylic acid tert-butyl ester

HRID 2277733ノート

反応式

HRID 2277733 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][CH:14]=2)([F:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:22][C:23]1[CH:24]=[C:25]([C:30](=[O:35])[C:31]([F:34])([F:33])[F:32])[CH:26]=[C:27]([Cl:29])[CH:28]=1.C(N(CC)CC)C>CCCCCCC>[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]([C:19](=[O:21])[CH2:20][C:30]([C:25]3[CH:26]=[C:27]([Cl:29])[CH:28]=[C:23]([Cl:22])[CH:24]=3)([OH:35])[C:31]([F:34])([F:33])[F:32])=[CH:17][CH:18]=2)([F:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 27582311-(3,5-Dichlorophenyl)-2,2,2-trifluoroethan-1-oneHCID 716803193-(4-Acetyl-phenyl)-3-fluoro-azetidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 897255463-{4-[3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-3-hydroxy-butyryl]-phenyl}-3-fluoro-azetidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 8900Heptane溶媒

反応条件

温度
60 °C

実験手順

In a clean and dry seal tube, to a stirred solution of 3-(4-acetyl-phenyl)-3-fluoro-azetidine-1-carboxylic acid tert-butyl ester (4 g, 13.652 mmol, 1eq.) in heptane (40 mL) was added 1-(3,5-dichlorophenyl)-2,2,2-trifluro-ethanone (6.60 gm, 27.304 mmol, 2eq.) followed by addition of triethyl amine (TEA, 3.80 ml, 27.304 mmol, 2eq.) at room temperature. Resulting reaction mixture was heated at 60° C. for 16 hours. After maximum consumption of starting material, reaction mixture was cooled to room temperature, solid precipitated out. Solid was filtered over Buchner funnel and washed with heptane (2×30 mL) and n-Pentane (70 mL) and dried under reduced pressure to get product as white solid. Yield: −5.0 g (68.31%). 1H NMR (400 MHz, CDCl3) δ: 1.47 (s, 9H), 3.68 (d, J=17.36 Hz, 1H), 3.85 (d, J=17.44 Hz, 1H), 4.17-4.24 (m, 2H), 4.39-4.47 (m, 2H), 5.69 (s, 1H), 7.33-7.35 (m, 1H), 7.48 (d, J=1.16 Hz, 2H), 7.62 (d, J=8.44 Hz, 2H), 7.98 (d, J=8.28 Hz, 2H). LC-MS (m/z): =534.0 (M−H).

後処理

  1. customIn a clean and dry
  2. customseal tube
  3. customResulting
  4. customreaction mixture
  5. customAfter maximum consumption of starting material, reaction mixture
  6. temperaturewas cooled to room temperature
  7. customsolid precipitated out
  8. filtrationSolid was filtered over Buchner funnel
  9. washwashed with heptane (2×30 mL) and n-Pentane (70 mL)
  10. customdried under reduced pressure
  11. customto get product as white solid

出典と根拠

ORDレコード
ord-6c1bff4eed6944feba0e8725af124895
出典データセット
uspto-grants-2015_09
特許番号
US09133172B2

反応ノート

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