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

HRID 130598노트

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HRID 130598 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-3895e331c8d948d79438e421802a7a6a
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381818B2

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