Dichloroacetic Acid → HCID 59289330, 화합물

HRID 2191034노트

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HRID 2191034 반응식
O[CH2:2][C@@H:3]1[C@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@H:6]2[C@H:5]([N:13]2[C:17]3=[N:18][CH:19]=[N:20][C:21]([NH:22][C:23](=[O:30])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[C:16]3[CH:15]=[N:14]2)[O:4]1.ClC(Cl)C(O)=O.C1CCC(N=C=NC2CCCCC2)CC1.[CH2:52]([O:54][P:55]([CH:60]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:57][CH2:58][CH3:59])=[O:56])[CH3:53]>CS(C)=O.O.CO>[C:23]([NH:22][C:21]1[N:20]=[CH:19][N:18]=[C:17]2[N:13]([C@H:5]3[C@@H:6]4[O:10][C:9]([CH3:12])([CH3:11])[O:8][C@@H:7]4[C@@H:3](/[CH:2]=[CH:60]/[P:55](=[O:56])([O:57][CH2:58][CH3:59])[O:54][CH2:52][CH3:53])[O:4]3)[N:14]=[CH:15][C:16]=12)(=[O:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

참가 물질

8

반응물 4

HCID 6597Dichloroacetic AcidHCID 10868DicyclohexylcarbodiimideHCID 10573715Diethyl(triphenylphosphoranylidene)methylphosphonateHCID 59289350HCID 59289350, 화합물

생성물 1

HCID 59289330HCID 59289330, 화합물수율 27%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 887Methanol용매HCID 962Water용매

실험 절차

Compound 22.3 (2.03 g, 4.93 mmol) in anhydrous dimethyl sulfoxide (25 mL, 0.2 M) was treated with dichloroacetic acid (400 μL, 4.93 mmol) and DCC (2.04 g, 9.67 mmol). The solution was stirred at room temperature for 2 h. [(Diethoxyphosphinyl)methylidene]triphenylphosphorane (2.0 g, 4.93 mmol, J. Org. Chem. 1996, 61, 7697-7701) was added and the mixture was stirred overnight. MeOH (25 mL) and H2O (25 mL) were added and the mixture was filtered over a plug of SiO2 and washed with MeOH (3×25 mL). The solvent was removed in vacuo and residue was suspended in CH2Cl2 and filtered over a plug of SiO2, and the solvent removed in vacuo. The residue was subjected to a column chromatography eluting with 0-100% EtOAc-hexanes, followed by 0-20% MeOH—CH2Cl2 to afford compound 22.4 (734 mg, 27% yield, E/Z ratio not determined) as a white solid (data for major isomer): 1H NMR (CDCl3, 300 MHz) 9.73 (br s, 1H), 8.71 (s, 2H), 7.91 (d, J=7.8 Hz, 2H), 7.50 (m, 1H), 7.35 (t, J=7.5 Hz, 2H), 6.89 (m, 1H), 6.15 (br s, 1H), 5.95 (m, 1H), 4.78 (m, 1H), 4.62 (m, 1H), 4.36 (m, 1H), 4.01 (m, 4H), 1.23 (m, 12H); 31P NMR (DMSO-d6, 121.4 MHz) 15.9; MS (ESI) m/z 544 [M+H+].

후처리

  1. additionwas added
  2. filtrationthe mixture was filtered over a plug of SiO2
  3. washwashed with MeOH (3×25 mL)
  4. customThe solvent was removed in vacuo and residue
  5. filtrationfiltered over a plug of SiO2
  6. customthe solvent removed in vacuo
  7. washeluting with 0-100% EtOAc-hexanes

출처 및 근거

ORD 기록
ord-333793ed727c42829d876d7693e85eee
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324179B2

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