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Dimethylformamide → Methyl 3-[5-(1,2-dithiolan-3-yl)pentyl]ureidoacetate

HRID 849585
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HRID 849585 반응식
[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]C(O)=O)[S:2]1.Cl.[CH3:15][O:16][C:17](=[O:20])[CH2:18][NH2:19].C[N:22](C)[CH:23]=[O:24]>C1(C)C=CC=CC=1.C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:22][C:23](=[O:24])[NH:19][CH2:18][C:17]([O:16][CH3:15])=[O:20])[S:2]1
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참가 물질

7

반응물 3

HCID 6228DimethylformamideHCID 122755Glycine methyl ester hydrochlorideHCID 226203646-(1,2-Dithiolan-3-yl)hexanoic acid

생성물 1

HCID 18358079Methyl 3-[5-(1,2-dithiolan-3-yl)pentyl]ureidoacetate

시약·촉매·용매 3

HCID 1140Toluene용매2회HCID 8471Triethylamine
용매
HCID 199401P,P-Diphenylphosphinic azide용매

실험 절차

The reaction was carried out as described in Example 46, but using 10 ml of a solution of 1.5 mmol of 6-(1,2-dithiolan-3-yl)hexanoic acid (prepared as described in Example 104) in toluene, 6 ml of anhydrous toluene, 0.42 ml of triethylamine, 0.39 ml of diphenylphosphoryl azide, 6 ml of anhydrous dimethylformamide and 254 mg of glycine methyl ester hydrochloride. The solvent was removed from the reaction mixture by evaporation under reduced pressure, and water was added to the residue, after which it was extracted with ethyl acetate. The extraction solution was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The ethyl acetate was removed from the extraction solution by evaporation under reduced pressure, and the residue was subjected to silica gel column chromatography, using 1:4 and 3:2 by volume mixtures of ethyl acetate and hexane as the eluent. The solvent was removed from the eluate by evaporation under reduced pressure, and the residue was dissolved in dioxane and then lyophilised, to obtain 16 mg of the title compound as yellow crystals having an Rf value of 0.62 (silica gel thin layer chromatography; using a 2:3 by volume mixture of ethyl acetate and hexane as developing solvent).

후처리

  1. customThe solvent was removed from the reaction mixture by evaporation under reduced pressure, and water
  2. additionwas added to the residue
  3. extractionafter which it was extracted with ethyl acetate
  4. washThe extraction solution was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe ethyl acetate was removed from the extraction solution by evaporation under reduced pressure
  7. customThe solvent was removed from the
  8. customeluate by evaporation under reduced pressure
  9. dissolutionthe residue was dissolved in dioxane

출처 및 근거

ORD 기록
ord-972d59fa65104d8a8e4735c3e1b700fa
출처 데이터셋
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06013663

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