Pentafluorophenyl Trifluoroacetate → 3-[(tert-Butyl)oxycarbonyl]propyl 2,3,4,5,6-pentafluorophenyl butane-1,4-dioate

HRID 2356301ノート

反応式

HRID 2356301 の反応式
[C:1]([O:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=[O:14])[CH2:2]CC(OCC1C=CC=CC=1)=O.F[C:27](F)(F)[C:28]([O:30][C:31]1[C:36]([F:37])=[C:35]([F:38])[C:34]([F:39])=[C:33]([F:40])[C:32]=1[F:41])=[O:29]>C1COCC1.[Pd]>[C:1]([O:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=[O:14])[CH2:2][CH2:27][C:28]([O:30][C:31]1[C:36]([F:37])=[C:35]([F:38])[C:34]([F:39])=[C:33]([F:40])[C:32]=1[F:41])=[O:29]

参加物

5

反応物 2

HCID 4327891Pentafluorophenyl TrifluoroacetateHCID 597306963-[(tert-Butyl)oxycarbonyl]propyl phenylmethyl butane-1,4-dioate

生成物 1

HCID 597306583-[(tert-Butyl)oxycarbonyl]propyl 2,3,4,5,6-pentafluorophenyl butane-1,4-dioate収率 91%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Compound 3 (2.0 g, 5.7 mmol) was hydrogenated for 20 h at 40 psi in THF (100 mL) in the presence of 0.2 g of 10% Pd/C. The catalyst was removed by filtration through Celite and filtrate concentrated. The acid was dissolved in 20 mL of anhydrous CH2Cl2. Diisopropylethylamine ((0.88 g, 6.8 mmol) was added followed by pentafluorophenyl trifluoroacetate (1.9 g, 6.8 mmol). After being kept at room temperature for 1 h solvent was evaporated and residue chromatographed on silica (ethyl acetate-hexane) to afford 2.2 g (91%) of 4 as viscous liquid. 1H NMR (DMSO-d6) δ 4.05 (t, J=6 Hz, 2H), 3.04 (t, J=6 Hz, 2H), 2.72 (t, J=6 Hz, 2H), 2.26 (t, J=7 Hz, 2H), 1.78 (q, 2H), 1.38 (s, 9H).

後処理

  1. customThe catalyst was removed by filtration through Celite and filtrate
  2. concentrationconcentrated
  3. dissolutionThe acid was dissolved in 20 mL of anhydrous CH2Cl2
  4. additionDiisopropylethylamine ((0.88 g, 6.8 mmol) was added
  5. customsolvent was evaporated
  6. customresidue chromatographed on silica (ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-1db908cf5adf43e8b37a7742e4d6e9da
出典データセット
uspto-grants-2010_07
特許番号
US07759126B2

反応ノート

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