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Dicyclohexylcarbodiimide → 4-(Acetylamino)benzoic acid, 4-(4-((6-chloro-2-quinoxalinyl)oxy)phenoxy)-2-pentenyl ester

HRID 569009
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HRID 569009 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][C:13]1[CH:25]=[CH:24][C:16]([O:17][CH:18]([CH3:23])[CH:19]=[CH:20][CH2:21][OH:22])=[CH:15][CH:14]=1)[CH:6]=[N:5]2.[C:26]([NH:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=1)(=[O:28])[CH3:27].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.CN(C)C=O.CCOCC.O>[C:26]([NH:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([O:22][CH2:21][CH:20]=[CH:19][CH:18]([O:17][C:16]2[CH:15]=[CH:14][C:13]([O:12][C:7]3[CH:6]=[N:5][C:4]4[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=4)[N:8]=3)=[CH:25][CH:24]=2)[CH3:23])=[O:35])=[CH:32][CH:31]=1)(=[O:28])[CH3:27]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 19266p-Acetamidobenzoic acidHCID 542751324-(4-((6-Chloro-2-quinoxalinyl)oxy)phenoxy)2-penten-1-ol

생성물 1

HCID 571706794-(Acetylamino)benzoic acid, 4-(4-((6-chloro-2-quinoxalinyl)oxy)phenoxy)-2-pentenyl ester수율 27.6%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine
촉매
HCID 962Water용매
HCID 3283Diethyl Ether용매
HCID 6228Dimethylformamide용매

실험 절차

A mixture of 1.5 g (4.2 mmol) of the pentenol obtained in Example 3 above, 0.82 g (4.6 mmol) of 4-(acetylamino)benzoic acid, 0.95 g (4.6 mmol) of dicyclohexylcarbodiimide and 0.05 g of 4-(dimethylamino)pyridine in 20 ml of dimethylformamide was stirred at room temperature for 72 hours. The mixture was diluted with ether and water and filtered. The filtrates were separated, and the organic layer washed with saturated aqueous NaHCO3 and water, dried over MgSO4 and evaporated to dryness. The residue was purified by preparative scale HPLC, eluting with a 65:35 hexane:acetone mixture to give 0.6 g of the desired product as a pale yellow, glassy solid, m.p. 62°-68° C. (Compound 30).

후처리

  1. filtrationfiltered
  2. customThe filtrates were separated
  3. washthe organic layer washed with saturated aqueous NaHCO3 and water
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe residue was purified by preparative scale HPLC
  7. washeluting with a 65:35 hexane

출처 및 근거

ORD 기록
ord-0e417d4700ac4167b97bd1b547a4ae66
출처 데이터셋
uspto-grants-1988_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04731108

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