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Triethylamine → Acetic acid 2-acetoxy-1-{3-chlorocarbonyl-5-[(2,2-dimethyl-[1,3]-dioxolan-4-ylmethyl)-(2-hydroxy-ethyl)-carbamoyl]-2,4,6-triiodo-phenylcarbamoyl}-ethyl ester

HRID 219501
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HRID 219501 반응식
[C:1]([O:4][CH2:5][CH:6]([O:25][C:26](=[O:28])[CH3:27])[C:7](=[O:24])[NH:8][C:9]1[C:14]([I:15])=[C:13]([C:16](Cl)=[O:17])[C:12]([I:19])=[C:11]([C:20]([Cl:22])=[O:21])[C:10]=1[I:23])(=[O:3])[CH3:2].[CH3:29][C:30]1([CH3:40])[O:34][CH:33]([CH2:35][NH:36][CH2:37][CH2:38][OH:39])[CH2:32][O:31]1.C(N(CC)CC)C>CC(N(C)C)=O>[C:1]([O:4][CH2:5][CH:6]([O:25][C:26](=[O:28])[CH3:27])[C:7](=[O:24])[NH:8][C:9]1[C:14]([I:15])=[C:13]([C:16](=[O:17])[N:36]([CH2:35][CH:33]2[CH2:32][O:31][C:30]([CH3:40])([CH3:29])[O:34]2)[CH2:37][CH2:38][OH:39])[C:12]([I:19])=[C:11]([C:20]([Cl:22])=[O:21])[C:10]=1[I:23])(=[O:3])[CH3:2]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 205536662-[(2,2-Dimethyl-[1,3]dioxolan-4-yl-methyl)-amino]-ethanolHCID 59413986Acetic acid 2-acetoxy-1-(3,5-bis-chlorocarbonyl-2,4,6-triiodo-phenylcarbamoyl)-ethyl ester

생성물 1

HCID 59470592Acetic acid 2-acetoxy-1-{3-chlorocarbonyl-5-[(2,2-dimethyl-[1,3]-dioxolan-4-ylmethyl)-(2-hydroxy-ethyl)-carbamoyl]-2,4,6-triiodo-phenylcarbamoyl}-ethyl ester수율 38.5%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매2회

실험 절차

To a ice cooled solution of acetic acid 2-acetoxy-1-(3,5-bis-chlorocarbonyl-2,4,6-triiodo-phenylcarbamoyl)-ethyl ester (20 g, 0.026 mol) in anhydrous DMAC (20 ml) were added dropwise a solution of 2-[(2,2-Dimethyl-[1,3]dioxolan-4-yl-methyl)-amino]-ethanol (4.6 g, 0.026 mol) in DMAC (20 mL) followed by triethylamine (˜3 g). The mixture was stirred at room temperature for 24 h and then poured over icewater (0.75 litre). A white precipitate formed. This was collected and washed with cold water. The filter cake was then dissolved in ethyl acetate and washed with brine. The organics were collected, dried over MgSO4, filtered and evaporated to dryness. The product was purified by silica column chromatography eluting with Petroleum ether/ethyl acetate. Two peaks closely eluting at 80% ethyl acetate were analysed by NMR and mass spec, and show to both contain the desired material. These were combined post analysis to give the desired product (10 mmol, Yield=38%). The structure was confirmed by Mass Spec (ESI) m/z: Calculated for C23H26Cl I3N2O10 [M+H]+906.64. Found 906.93. 1H NMR (CDCl3; 300 MHz) δ=1.33 (2s, 3H) 1.45 (2s, 3H) 2.02 (s, 3H) 2.26 (s, 3H) 3-3.5 (m, 4H) 3.5-3.9 (m, 3H) 3.9-4.3 (m, 2H) 4.5 (m, 1H) 4.6-4.8 (m, 2H) 5.62 (NH singlet, 1H)

후처리

  1. additionpoured over icewater (0.75 litre)
  2. customA white precipitate formed
  3. customThis was collected
  4. washwashed with cold water
  5. dissolutionThe filter cake was then dissolved in ethyl acetate
  6. washwashed with brine
  7. customThe organics were collected
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customThe product was purified by silica column chromatography
  12. washeluting with Petroleum ether/ethyl acetate
  13. washTwo peaks closely eluting at 80% ethyl acetate

출처 및 근거

ORD 기록
ord-180f03b2ce8348499f19f262f2bf64cd
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08202511B2

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