Tributylphosphine → HCID 66764153, 화합물

HRID 921999

반응식

HRID 921999 반응식
[Cl:1][CH2:2][C:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1)=[O:4].[CH2:16]([P:20]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19]>C(OCC)(=O)C>[Cl-:1].[C:13]([NH:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][C:3](=[O:4])[CH2:2][P+:20]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:7][CH:8]=1)(=[O:15])[CH3:14]

참가 물질

4

반응물 2

HCID 13831TributylphosphineHCID 132776644-Acetamidophenyl chloroacetate

생성물 1

HCID 66764153HCID 66764153, 화합물수율 65%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

4-Acetamidophenyl 2-chloroacetate [2] (1.138 g, 5 mmol) and tributylphosphine (0.475 g, 6 mmol) were suspended in 50 ml of anhydrous ethyl acetate and refluxed for 48 hrs. After cooling to room temperature the white precipitate was filtered, washed with ethylacetate and diethylether and dried under reduced pressure to give [6]. The crude product was crystallized twice from acetonitrile to give pure [6] in 65% yield. Identity and purity was confirmed via 1H and 13C NMR. The desired compound is isolated as colourless needles. 1H-NMR (300 MHz, d6-DMSO) δ(ppm)=10.49 (s, 1H), 7.71 (d, J=8.95 Hz, 2H), 7.12 (d, J=8.95 Hz, 2H), 4.18 (d, J=14.33, 2H), 2.41 (m, 3H), 2.06 (s, 3H), 1.55 (m, 6H), 1.41 (m, 6H), 0.91 (t, J=7.17). 31P-NMR (121.5 MHz, d6-DMSO) δ(ppm)=34.8. 13C-NMR (75 MHz, d6-DMSO) δ(ppm)=168.4, 164.7, 144.8, 137.8, 121.4, 119.9, 25.8 (d, J=47.9 Hz), 23.9, 23.3 (d, J=16.77 Hz), 22.6 (d, J=4.43 Hz), 18.2 (d, J=47.7 Hz), 13.2. mp 199° C. (dec), T5%onset 197° C.

후처리

  1. temperaturerefluxed for 48 hrs
  2. filtrationwas filtered
  3. washwashed with ethylacetate and diethylether
  4. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-3b86c66b24b64d1b8e6328e38ca4601f
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278134B2

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